Renewable Rigid Diamines: Efficient, Stereospecific Synthesis of High Purity Isohexide Diamines
We report an efficient three‐step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6‐dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high‐perfor...
Saved in:
| Published in | ChemSusChem Vol. 4; no. 12; pp. 1823 - 1829 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
16.12.2011
WILEY‐VCH Verlag |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | We report an efficient three‐step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6‐dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high‐performance biobased polymers, such as polyamides and polyurethanes. Among the three possible stereo‐isomers, dideoxy‐diamino isoidide and dideoxy‐diamino isosorbide can be synthesized from isomannide and isosorbide respectively in high yield with absolute stereo control. Furthermore, by using this methodology dideoxy‐amino isomannide—a tricyclic adduct—was obtained starting from isoidide in high yield. Our improved synthetic route is a valuable advance towards meeting scale and purity demands for evaluating the properties of new biobased performance materials, which will benefit the development of these plastics.
Turning up the stereo: An efficient three‐step strategy for synthesizing chiral biobased dideoxy‐diamino isoidide and dideoxy‐diamino isosorbide in high yield with absolute stereo control is described. These highly interesting chiral building blocks are presently the subject of several investigations due to their application in high‐performance biobased polymers such as polyamides and polyurethanes. |
|---|---|
| AbstractList | We report an efficient three‐step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6‐dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high‐performance biobased polymers, such as polyamides and polyurethanes. Among the three possible stereo‐isomers, dideoxy‐diamino isoidide and dideoxy‐diamino isosorbide can be synthesized from isomannide and isosorbide respectively in high yield with absolute stereo control. Furthermore, by using this methodology dideoxy‐amino isomannide—a tricyclic adduct—was obtained starting from isoidide in high yield. Our improved synthetic route is a valuable advance towards meeting scale and purity demands for evaluating the properties of new biobased performance materials, which will benefit the development of these plastics.
Turning up the stereo: An efficient three‐step strategy for synthesizing chiral biobased dideoxy‐diamino isoidide and dideoxy‐diamino isosorbide in high yield with absolute stereo control is described. These highly interesting chiral building blocks are presently the subject of several investigations due to their application in high‐performance biobased polymers such as polyamides and polyurethanes. We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high-performance biobased polymers, such as polyamides and polyurethanes. Among the three possible stereo-isomers, dideoxy-diamino isoidide and dideoxy-diamino isosorbide can be synthesized from isomannide and isosorbide respectively in high yield with absolute stereo control. Furthermore, by using this methodology dideoxy-amino isomannide—a tricyclic adduct—was obtained starting from isoidide in high yield. Our improved synthetic route is a valuable advance towards meeting scale and purity demands for evaluating the properties of new biobased performance materials, which will benefit the development of these plastics. We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high-performance biobased polymers, such as polyamides and polyurethanes. Among the three possible stereo-isomers, dideoxy-diamino isoidide and dideoxy-diamino isosorbide can be synthesized from isomannide and isosorbide respectively in high yield with absolute stereo control. Furthermore, by using this methodology dideoxy-amino isomannide-a tricyclic adduct-was obtained starting from isoidide in high yield. Our improved synthetic route is a valuable advance towards meeting scale and purity demands for evaluating the properties of new biobased performance materials, which will benefit the development of these plastics.We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high-performance biobased polymers, such as polyamides and polyurethanes. Among the three possible stereo-isomers, dideoxy-diamino isoidide and dideoxy-diamino isosorbide can be synthesized from isomannide and isosorbide respectively in high yield with absolute stereo control. Furthermore, by using this methodology dideoxy-amino isomannide-a tricyclic adduct-was obtained starting from isoidide in high yield. Our improved synthetic route is a valuable advance towards meeting scale and purity demands for evaluating the properties of new biobased performance materials, which will benefit the development of these plastics. |
| Author | Gootjes, Linda Vogelzang, Willem van Es, Daan S. van Haveren, Jacco Lutz, Martin Thiyagarajan, Shanmugam |
| Author_xml | – sequence: 1 givenname: Shanmugam surname: Thiyagarajan fullname: Thiyagarajan, Shanmugam organization: Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011 – sequence: 2 givenname: Linda surname: Gootjes fullname: Gootjes, Linda organization: Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011 – sequence: 3 givenname: Willem surname: Vogelzang fullname: Vogelzang, Willem organization: Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011 – sequence: 4 givenname: Jacco surname: van Haveren fullname: van Haveren, Jacco organization: Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011 – sequence: 5 givenname: Martin surname: Lutz fullname: Lutz, Martin organization: Bijvoet Center for Biomolecular Research, Crystal and Structural Chemistry, Utrecht University, Padualaan 8, 3584, Utrecht (The Netherlands) – sequence: 6 givenname: Daan S. surname: van Es fullname: van Es, Daan S. email: daan.vanes@wur.nl organization: Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22121062$$D View this record in MEDLINE/PubMed |
| BookMark | eNqFkc2P0zAQxS20iP2AK0eUGxdS7Dix472hsl_SLqAtaLmNXGfSDqROsRN1-9-TqN0KISEuM2Pr_d7IfqfsyLceGXst-ERwnr13MbpJxsVwkKZ8xk5EqfK0UPn3o8MsxTE7jfEH54obpV6w4ywTmeAqO2Fwjx43dt5gck8LqpKPZFfkMZ4nF3VNjtB375JZhwHbuEZHw10y2_puiZFi0tbJNS2WyZc-ULdNbmK7xEeq8GDzkj2vbRPx1b6fsW-XF1-n1-nt56ub6Yfb1OVSlmnhrBRSuKq2tsy1rCTmWgujhCkKjZXAMlNKm9q40nLpykIYLCtR1GYQay3P2PnOd2MX6MkPBbwNjiK0lqChebBhC5s-gG_Gtu7nEfLBnmcD_HYHr0P7q8fYwYqiw6axHts-ghHCZKXMxzVv9sp-vsIK1oFWo-_Thw6CfCdwoY0xYA2OOttR67tgqQHBYcwNxtzgkNuATf7Cnpz_CZj9e6nB7X_UMJ3Npn-y6Y6l2OHjgbXhJygtdQEPn67AKH15d1fO4EH-Bttvuys |
| CitedBy_id | crossref_primary_10_1016_j_mcat_2019_110539 crossref_primary_10_1021_cr3001274 crossref_primary_10_1039_D5SU00011D crossref_primary_10_1016_j_polymer_2021_123799 crossref_primary_10_7569_JRM_2013_634116 crossref_primary_10_1016_j_eurpolymj_2015_10_032 crossref_primary_10_1016_j_reactfunctpolym_2013_01_002 crossref_primary_10_1039_D1RA09196D crossref_primary_10_1021_acssuschemeng_2c07501 crossref_primary_10_1002_ejoc_201901661 crossref_primary_10_1021_ma302126b crossref_primary_10_1016_j_eurpolymj_2015_07_011 crossref_primary_10_1021_ma301091a crossref_primary_10_1002_cctc_201501077 crossref_primary_10_1002_pola_26833 crossref_primary_10_1021_acssuschemeng_8b03587 crossref_primary_10_1021_ma302209f crossref_primary_10_1039_D0GC03172K crossref_primary_10_1002_cssc_201300126 crossref_primary_10_1039_C4RA07896A crossref_primary_10_7569_JRM_2012_634108 crossref_primary_10_1021_acs_chemrev_5b00354 crossref_primary_10_1039_C5PY00521C crossref_primary_10_3390_molecules26237322 crossref_primary_10_1002_cssc_201700617 crossref_primary_10_1021_acscatal_2c01717 crossref_primary_10_1021_acsmedchemlett_2c00476 crossref_primary_10_1021_acssuschemeng_1c01266 crossref_primary_10_1021_acs_chemrev_6b00486 crossref_primary_10_1039_D1GC00955A crossref_primary_10_1002_cctc_201300284 crossref_primary_10_1002_ejoc_201600186 crossref_primary_10_1016_j_eurpolymj_2015_01_040 crossref_primary_10_1002_cssc_201200714 crossref_primary_10_1039_D2RA05710G crossref_primary_10_1021_sc500478f crossref_primary_10_1016_j_ica_2020_120094 crossref_primary_10_1007_s11998_016_9783_7 crossref_primary_10_1002_cssc_201900737 crossref_primary_10_1016_j_polymer_2015_07_051 crossref_primary_10_1021_acsmacrolett_9b00570 crossref_primary_10_3390_polym9110569 crossref_primary_10_1021_ma300782h crossref_primary_10_1002_cctc_201300407 crossref_primary_10_1039_C3RA42457J |
| Cites_doi | 10.1021/ja01594a055 10.1002/1521-3757(20010601)113:11<2056::AID-ANGE2056>3.0.CO;2-W 10.1107/S0108767307043930 10.1002/pola.1995.080331615 10.1002/star.19840360506 10.1002/macp.1997.021981013 10.1002/ange.201103199 10.1016/j.crci.2010.11.011 10.1007/BF00254275 10.1016/j.tet.2010.11.031 10.1016/j.tet.2005.02.010 10.1021/cr100352k 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 10.1002/(SICI)1097-4628(20000711)77:2<338::AID-APP9>3.0.CO;2-C 10.1080/00397918908051042 10.1039/jr9500000371 10.1016/j.progpolymsci.2009.10.001 10.1002/macp.1991.021920922 10.1039/jr9460000393 10.1016/0040-4020(80)80155-4 10.1016/S0008-6215(00)84675-3 10.1021/ma200256v 10.1107/S090744490804362X 10.1002/anie.201103199 10.1002/cssc.201100076 |
| ContentType | Journal Article |
| Copyright | Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Wageningen University & Research |
| Copyright_xml | – notice: Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim – notice: Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. – notice: Wageningen University & Research |
| DBID | BSCLL AAYXX CITATION CGR CUY CVF ECM EIF NPM 7X8 QVL |
| DOI | 10.1002/cssc.201100398 |
| DatabaseName | Istex CrossRef Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed MEDLINE - Academic NARCIS:Publications |
| DatabaseTitle | CrossRef MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) MEDLINE - Academic |
| DatabaseTitleList | MEDLINE - Academic CrossRef MEDLINE |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1864-564X |
| EndPage | 1829 |
| ExternalDocumentID | oai_library_wur_nl_wurpubs_419502 22121062 10_1002_cssc_201100398 CSSC201100398 ark_67375_WNG_967FMM8S_W |
| Genre | article Research Support, Non-U.S. Gov't Journal Article |
| GrantInformation_xml | – fundername: Dutch Polymer Institute funderid: 653 |
| GroupedDBID | --- 05W 0R~ 1OC 29B 33P 4.4 5GY 5VS 66C 77Q 8-1 A00 AAESR AAHHS AAIHA AANLZ AASGY AAXRX AAZKR ABCUV ACAHQ ACBWZ ACCFJ ACCZN ACGFS ACIWK ACPOU ACXBN ACXQS ADKYN ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AENEX AEQDE AEUYR AFBPY AFFPM AFZJQ AHBTC AHMBA AITYG AIURR AIWBW AJBDE ALMA_UNASSIGNED_HOLDINGS ALUQN AMYDB AZVAB BDRZF BFHJK BRXPI BSCLL CS3 DCZOG DR2 DRFUL DRSTM DU5 EBS EJD F5P FEDTE G-S GODZA HGLYW HVGLF HZ~ IX1 LATKE LAW LEEKS LH4 LITHE LOXES LUTES LW6 LYRES MEWTI MY~ O9- OIG P2W P4E PQQKQ ROL SUPJJ W99 WBKPD WOHZO WXSBR WYJ XV2 ZZTAW ~S- AAHQN AAMNL AANHP AAYCA ACRPL ACYXJ ADNMO AFWVQ ALVPJ AAYXX AEYWJ AGQPQ AGYGG CITATION CGR CUY CVF ECM EIF NPM 7X8 AAMMB AEFGJ AGXDD AIDQK AIDYY - 0R 31 53G ACDCL ADDAD AEUQT EBD HZ MRJOP MSJOP MXJOP MY PQEST QVL RIG S- SV3 UNR XFK |
| ID | FETCH-LOGICAL-c4338-5ca3131cdfaa8473d3e47719619557ed1e826679f9c8a03c8519e8d15f973d773 |
| IEDL.DBID | DR2 |
| ISSN | 1864-5631 1864-564X |
| IngestDate | Thu Feb 04 15:47:33 EST 2021 Fri Jul 11 06:12:33 EDT 2025 Wed Feb 19 01:49:01 EST 2025 Thu Apr 24 23:12:31 EDT 2025 Tue Jul 01 03:55:16 EDT 2025 Wed Jan 22 16:40:16 EST 2025 Wed Oct 30 10:03:43 EDT 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 12 |
| Language | English |
| License | Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c4338-5ca3131cdfaa8473d3e47719619557ed1e826679f9c8a03c8519e8d15f973d773 |
| Notes | ArticleID:CSSC201100398 Dutch Polymer Institute - No. 653 istex:C739519E030F6BD77F4A230790678236ED307C43 ark:/67375/WNG-967FMM8S-W ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 22121062 |
| PQID | 911928347 |
| PQPubID | 23479 |
| PageCount | 7 |
| ParticipantIDs | wageningen_narcis_oai_library_wur_nl_wurpubs_419502 proquest_miscellaneous_911928347 pubmed_primary_22121062 crossref_citationtrail_10_1002_cssc_201100398 crossref_primary_10_1002_cssc_201100398 wiley_primary_10_1002_cssc_201100398_CSSC201100398 istex_primary_ark_67375_WNG_967FMM8S_W |
| ProviderPackageCode | CITATION AAYXX QVL |
| PublicationCentury | 2000 |
| PublicationDate | December 16, 2011 |
| PublicationDateYYYYMMDD | 2011-12-16 |
| PublicationDate_xml | – month: 12 year: 2011 text: December 16, 2011 day: 16 |
| PublicationDecade | 2010 |
| PublicationPlace | Weinheim |
| PublicationPlace_xml | – name: Weinheim – name: Germany |
| PublicationTitle | ChemSusChem |
| PublicationTitleAlternate | ChemSusChem |
| PublicationYear | 2011 |
| Publisher | WILEY-VCH Verlag WILEY‐VCH Verlag |
| Publisher_xml | – name: WILEY-VCH Verlag – name: WILEY‐VCH Verlag |
| References | J. Thiem, Makromol. Chem. 1986, 187, 2775-2785 J. Thiem, H. Lüders, Polym. Bull. 1984, 11, 365-369. C. A. G. Haasnoot, F. A. A. M. DeLeeuw, C. Altona, Tetrahedron 1980, 36, 2783-2792. J. Kuszmann, G. Medgyes, Carbohydr. Res. 1980, 85, 259-269 H. R. Kricheldorf, Z. Gomourachvili, Macromol. Chem. Phys. 1997, 198, 3149 M. Okada, K. Tsunoda, K. Tachikawa, K. Aoi, J. Appl. Polym. Sci. 2000, 77, 338. Chem. Abstr. 2011, 154, 110159 M. Okada, Y. Okada, K. Aoi, J. Polym. Sci., Part A Polym. Chem. 1995, 33, 2813 A. C. Cope, T. Y. Shen, J. Am. Chem. Soc. 1956, 78, 3177-3182. J. Thiem, H. Lüders, Starch/Staerke 1984, 36, 170-176 J. Wu, P. Eduard, S. Thiyagarajan, J. van Haveren, D. van Es, C. E. Koning, M. Lutz, F. Célia Guerra, ChemSusChem 2011, 4, 599-603 Angew. Chem. Int. Ed. 2001, 40, 2004-2021. J. Thiem, F. Bachmann, Makromol. Chem. 1991, 192, 2163-2182. T. G. Archibald, K. Baum, Synth. Commun. 1989, 19, 1493-1498. Chem. Abstr. 2011, 154, 110160]. For safe handling of organic azides, (NC+NO)/NN>3, where NX=number of X atoms in the azide; isohexide diazide formulae amount to 8/6=1.3 (!); see also H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075 V. G. Bashford, L. F. Wiggins, J. Chem. Soc. 1950, 371-374. S. Kumar, U. Ramachandran, Tetrahedron 2005, 61, 4141-4148. G. O. Oleksandr, R. S. Dmytro, V. M. Dmitriy, T. A. Andrey, K. V. Komarov, Chem. Rev. 2011, 111, 5506-5568 P. Tundo, F. Aricò, G. Gauthier, A. Baldacci, C. R. Chimie 2011, 14, 652-655. S. Thiyagarajan, L. Gootjes, W. Vogelzang, J. Wu, J. van Haveren, D. van Es, Tetrahedron 2011, 67, 383-389. Angew. Chem. Int. Ed. 2011, 50, 7599-7603. F. Fenouillot, A. Rousseau, G. Colomines, R. Saint-Loup, J. P. Pascault, Prog. Polym. Sci. 2010, 35, 578-622. S. Imm, S. Bähn, M. Zhang, L. Neubert, H. Neumann, F. Klasovsky, J. Pfeffer, T. Haas, M. Beller, Angew. Chem. 2011, 123, 7741-7745 G. M. Sheldrick, Acta Crystallogr. Sec. A 2008, 64, 112-122. L. Jasinska, M. Villani, J. Wu, D. van Es, E. Klop, S. Rastogi, C. E. Koning, Macromolecules 2011, 44, 3458-3466 R. Montgomery, L. F. Wiggins, J. Chem. Soc. 1946, 393-396 Chem. Abstr. 2011, 154, 89176 A. L. Spek, Acta Crystallogr. Sec. D 2009, 65, 148-155. 2009; 65 2010; 35 1980; 85 2011 1997; 198 1995; 33 1991; 192 1956; 78 1986; 18 1950 2004 2011 2011; 123 50 2005; 61 2011; 14 2011; 4 2011; 111 1999 2011 2011; 154 1980; 36 1984; 36 2000 2001 2001; 113 40 1984; 11 2000; 77 1965 2011; 44 2011; 67 2008; 64 1989; 19 1946 e_1_2_6_31_2 e_1_2_6_30_2 (e_1_2_6_24_3) 2011; 154 (e_1_2_6_22_3) 2011; 154 (e_1_2_6_23_3) 2011; 154 e_1_2_6_18_2 e_1_2_6_12_2 e_1_2_6_34_3 e_1_2_6_35_2 e_1_2_6_13_2 e_1_2_6_34_2 e_1_2_6_10_2 e_1_2_6_32_3 e_1_2_6_33_2 e_1_2_6_11_2 e_1_2_6_32_2 e_1_2_6_16_2 e_1_2_6_39_2 e_1_2_6_17_2 e_1_2_6_38_2 e_1_2_6_14_2 e_1_2_6_37_2 e_1_2_6_15_2 e_1_2_6_36_2 e_1_2_6_42_2 e_1_2_6_20_2 e_1_2_6_41_2 e_1_2_6_40_2 e_1_2_6_8_2 e_1_2_6_7_2 e_1_2_6_9_2 e_1_2_6_29_2 e_1_2_6_4_2 e_1_2_6_3_2 e_1_2_6_6_2 e_1_2_6_5_2 e_1_2_6_24_2 e_1_2_6_23_2 e_1_2_6_2_2 e_1_2_6_22_2 e_1_2_6_1_2 e_1_2_6_21_2 Thiem J. (e_1_2_6_19_2) 1986; 18 e_1_2_6_28_2 e_1_2_6_43_2 e_1_2_6_27_2 e_1_2_6_26_2 e_1_2_6_25_2 |
| References_xml | – reference: V. G. Bashford, L. F. Wiggins, J. Chem. Soc. 1950, 371-374. – reference: J. Thiem, F. Bachmann, Makromol. Chem. 1991, 192, 2163-2182. – reference: G. O. Oleksandr, R. S. Dmytro, V. M. Dmitriy, T. A. Andrey, K. V. Komarov, Chem. Rev. 2011, 111, 5506-5568; – reference: P. Tundo, F. Aricò, G. Gauthier, A. Baldacci, C. R. Chimie 2011, 14, 652-655. – reference: F. Fenouillot, A. Rousseau, G. Colomines, R. Saint-Loup, J. P. Pascault, Prog. Polym. Sci. 2010, 35, 578-622. – reference: J. Thiem, Makromol. Chem. 1986, 187, 2775-2785; – reference: J. Thiem, H. Lüders, Starch/Staerke 1984, 36, 170-176; – reference: S. Thiyagarajan, L. Gootjes, W. Vogelzang, J. Wu, J. van Haveren, D. van Es, Tetrahedron 2011, 67, 383-389. – reference: J. Wu, P. Eduard, S. Thiyagarajan, J. van Haveren, D. van Es, C. E. Koning, M. Lutz, F. Célia Guerra, ChemSusChem 2011, 4, 599-603; – reference: J. Thiem, H. Lüders, Polym. Bull. 1984, 11, 365-369. – reference: Chem. Abstr. 2011, 154, 89176]; – reference: Chem. Abstr. 2011, 154, 110159]; – reference: C. A. G. Haasnoot, F. A. A. M. DeLeeuw, C. Altona, Tetrahedron 1980, 36, 2783-2792. – reference: S. Imm, S. Bähn, M. Zhang, L. Neubert, H. Neumann, F. Klasovsky, J. Pfeffer, T. Haas, M. Beller, Angew. Chem. 2011, 123, 7741-7745; – reference: For safe handling of organic azides, (NC+NO)/NN>3, where NX=number of X atoms in the azide; isohexide diazide formulae amount to 8/6=1.3 (!); see also H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; – reference: M. Okada, K. Tsunoda, K. Tachikawa, K. Aoi, J. Appl. Polym. Sci. 2000, 77, 338. – reference: R. Montgomery, L. F. Wiggins, J. Chem. Soc. 1946, 393-396; – reference: Angew. Chem. Int. Ed. 2001, 40, 2004-2021. – reference: Chem. Abstr. 2011, 154, 110160]. – reference: H. R. Kricheldorf, Z. Gomourachvili, Macromol. Chem. Phys. 1997, 198, 3149; – reference: L. Jasinska, M. Villani, J. Wu, D. van Es, E. Klop, S. Rastogi, C. E. Koning, Macromolecules 2011, 44, 3458-3466; – reference: T. G. Archibald, K. Baum, Synth. Commun. 1989, 19, 1493-1498. – reference: Angew. Chem. Int. Ed. 2011, 50, 7599-7603. – reference: G. M. Sheldrick, Acta Crystallogr. Sec. A 2008, 64, 112-122. – reference: S. Kumar, U. Ramachandran, Tetrahedron 2005, 61, 4141-4148. – reference: M. Okada, Y. Okada, K. Aoi, J. Polym. Sci., Part A Polym. Chem. 1995, 33, 2813; – reference: A. L. Spek, Acta Crystallogr. Sec. D 2009, 65, 148-155. – reference: A. C. Cope, T. Y. Shen, J. Am. Chem. Soc. 1956, 78, 3177-3182. – reference: J. Kuszmann, G. Medgyes, Carbohydr. Res. 1980, 85, 259-269; – volume: 4 start-page: 599 year: 2011 end-page: 603 publication-title: ChemSusChem – year: 2011 – volume: 111 start-page: 5506 year: 2011 end-page: 5568 publication-title: Chem. Rev. – volume: 77 start-page: 338 year: 2000 publication-title: J. Appl. Polym. Sci. – volume: 11 start-page: 365 year: 1984 end-page: 369 publication-title: Polym. Bull. – start-page: 371 year: 1950 end-page: 374 publication-title: J. Chem. Soc. – volume: 198 start-page: 3149 year: 1997 publication-title: Macromol. Chem. Phys. – volume: 35 start-page: 578 year: 2010 end-page: 622 publication-title: Prog. Polym. Sci. – volume: 14 start-page: 652 year: 2011 end-page: 655 publication-title: C. R. Chimie – volume: 154 start-page: 110160 year: 2011 2011 publication-title: Chem. Abstr. – year: 2000 – volume: 67 start-page: 383 year: 2011 end-page: 389 publication-title: Tetrahedron – volume: 61 start-page: 4141 year: 2005 end-page: 4148 publication-title: Tetrahedron – volume: 64 start-page: 112 year: 2008 end-page: 122 publication-title: Acta Crystallogr. Sec. A – volume: 36 start-page: 170 year: 1984 end-page: 176 publication-title: Starch/Staerke – volume: 154 start-page: 110159 year: 2011 2011 publication-title: Chem. Abstr. – volume: 113 40 start-page: 2056 2004 year: 2001 2001 end-page: 2075 2021 publication-title: Angew. Chem. Angew. Chem. Int. Ed. – volume: 192 start-page: 2163 year: 1991 end-page: 2182 publication-title: Makromol. Chem. – volume: 36 start-page: 2783 year: 1980 end-page: 2792 publication-title: Tetrahedron – volume: 44 start-page: 3458 year: 2011 end-page: 3466 publication-title: Macromolecules – volume: 154 start-page: 89176 year: 2011 2011 publication-title: Chem. Abstr. – volume: 18 start-page: 7 year: 1986 end-page: 2785 publication-title: Makromol. Chem. – volume: 65 start-page: 148 year: 2009 end-page: 155 publication-title: Acta Crystallogr. Sec. D – year: 1965 – year: 2004 – volume: 19 start-page: 1493 year: 1989 end-page: 1498 publication-title: Synth. Commun. – volume: 123 50 start-page: 7741 7599 year: 2011 2011 end-page: 7745 7603 publication-title: Angew. Chem. Angew. Chem. Int. Ed. – volume: 33 start-page: 2813 year: 1995 publication-title: J. Polym. Sci., Part A Polym. Chem. – volume: 78 start-page: 3177 year: 1956 end-page: 3182 publication-title: J. Am. Chem. Soc. – volume: 85 start-page: 259 year: 1980 end-page: 269 publication-title: Carbohydr. Res. – year: 1999 – start-page: 393 year: 1946 end-page: 396 publication-title: J. Chem. Soc. – ident: e_1_2_6_28_2 doi: 10.1021/ja01594a055 – ident: e_1_2_6_32_2 doi: 10.1002/1521-3757(20010601)113:11<2056::AID-ANGE2056>3.0.CO;2-W – ident: e_1_2_6_41_2 doi: 10.1107/S0108767307043930 – ident: e_1_2_6_5_2 – ident: e_1_2_6_13_2 doi: 10.1002/pola.1995.080331615 – ident: e_1_2_6_2_2 – ident: e_1_2_6_10_2 – ident: e_1_2_6_8_2 doi: 10.1002/star.19840360506 – ident: e_1_2_6_11_2 doi: 10.1002/macp.1997.021981013 – ident: e_1_2_6_34_2 doi: 10.1002/ange.201103199 – ident: e_1_2_6_38_2 doi: 10.1016/j.crci.2010.11.011 – ident: e_1_2_6_24_2 – ident: e_1_2_6_9_2 doi: 10.1007/BF00254275 – ident: e_1_2_6_33_2 doi: 10.1016/j.tet.2010.11.031 – ident: e_1_2_6_3_2 – volume: 18 start-page: 7 year: 1986 ident: e_1_2_6_19_2 publication-title: Makromol. Chem. – ident: e_1_2_6_6_2 – ident: e_1_2_6_36_2 doi: 10.1016/j.tet.2005.02.010 – ident: e_1_2_6_1_2 doi: 10.1021/cr100352k – ident: e_1_2_6_35_2 – ident: e_1_2_6_43_2 – ident: e_1_2_6_32_3 doi: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 – ident: e_1_2_6_12_2 – ident: e_1_2_6_15_2 – volume: 154 start-page: 110160 year: 2011 ident: e_1_2_6_24_3 publication-title: Chem. Abstr. – ident: e_1_2_6_14_2 doi: 10.1002/(SICI)1097-4628(20000711)77:2<338::AID-APP9>3.0.CO;2-C – ident: e_1_2_6_31_2 doi: 10.1080/00397918908051042 – ident: e_1_2_6_27_2 doi: 10.1039/jr9500000371 – ident: e_1_2_6_17_2 doi: 10.1016/j.progpolymsci.2009.10.001 – ident: e_1_2_6_23_2 – ident: e_1_2_6_20_2 doi: 10.1002/macp.1991.021920922 – ident: e_1_2_6_26_2 doi: 10.1039/jr9460000393 – ident: e_1_2_6_37_2 doi: 10.1016/0040-4020(80)80155-4 – ident: e_1_2_6_18_2 – volume: 154 start-page: 110159 year: 2011 ident: e_1_2_6_23_3 publication-title: Chem. Abstr. – ident: e_1_2_6_40_2 – ident: e_1_2_6_30_2 doi: 10.1016/S0008-6215(00)84675-3 – ident: e_1_2_6_29_2 – ident: e_1_2_6_21_2 doi: 10.1021/ma200256v – ident: e_1_2_6_22_2 – ident: e_1_2_6_42_2 doi: 10.1107/S090744490804362X – ident: e_1_2_6_39_2 – ident: e_1_2_6_4_2 – ident: e_1_2_6_34_3 doi: 10.1002/anie.201103199 – ident: e_1_2_6_7_2 – volume: 154 start-page: 89176 year: 2011 ident: e_1_2_6_22_3 publication-title: Chem. Abstr. – ident: e_1_2_6_16_2 doi: 10.1002/cssc.201100076 – ident: e_1_2_6_25_2 |
| SSID | ssj0060966 |
| Score | 2.2147648 |
| Snippet | We report an efficient three‐step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6‐dianhydrohexitols. These biobased chiral... We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral... |
| SourceID | wageningen proquest pubmed crossref wiley istex |
| SourceType | Open Access Repository Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 1823 |
| SubjectTerms | amines Bridged Bicyclo Compounds, Heterocyclic - chemistry chiral building-blocks chirality Conservation of Natural Resources derivatives Diamines - chemical synthesis isomers Isosorbide - chemistry Magnetic Resonance Spectroscopy polyamides polycondensation polycycles polyesters Polymers renewable resources resources Stereoisomerism X-Ray Diffraction |
| Title | Renewable Rigid Diamines: Efficient, Stereospecific Synthesis of High Purity Isohexide Diamines |
| URI | https://api.istex.fr/ark:/67375/WNG-967FMM8S-W/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcssc.201100398 https://www.ncbi.nlm.nih.gov/pubmed/22121062 https://www.proquest.com/docview/911928347 http://www.narcis.nl/publication/RecordID/oai:library.wur.nl:wurpubs%2F419502 |
| Volume | 4 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9QwELZQOVAO5Q3LSz4guJA2jl8xN7R0KUit0C5Ve7MS24FVq2y12dUWfj0zziZlEQgJTlEkeyTb8_iczHxDyAvPhXGpV2BpHC4oRZEnRaayxOdap5URJc-xdvjwSB0ci4-n8vSnKv6WH6L_4IaWEf01GnhRNntXpKGuaVyk4MTyUqz2xYQtREXjnj9KAT6P5UW5EolUnHWsjWm2tzl9Iypdxw2-_B3kvEm2V2Dmdax72oSzMR6NbpGiW0mbhnK2u1yUu-77LySP_7PU22RnDVbp21a77pBrob5Lbgy7HnH3iB2Dq1xh9RUdT79MPX2HdeLgPd_Q_chNASHtNZ3A2QWkJI_5f3TyrQbU2UwbOqso5pnQT7GFHv3QzL6Gy6kPvZj75Hi0_3l4kKxbNiROwGU3ka7gjDPnKzh1obnnQWgNVs6MlDp4FuA6o7SpjMuLlDvAeybknsnKwGCt-QOyVc_q8IjQNAQplckBMFYiKJRXeJlWLPehNCUbkKQ7MuvWfObYVuPctkzMmcVts_22DcirfvxFy-Txx5Evowb0w4r5Gea_aWlPjt5bo_ToENyRPRkQ2qmIhY3HXy1FHWbLxkIIMQDchB6Qh63q9MKyDDnbVDYg_EqXbI2doxqLZN9rjbCr5dzW5_gACY0V2LAXZmVRU_6yBDucTIb92-N_mfSEbMfv5yxLmHpKthbzZXgGAGxRPo9G9gMH-CeH |
| linkProvider | Wiley-Blackwell |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1bb9MwFLZge9h44H4JVz8geCFbHMd2zBvqVjpYK9RuGm9WEjtQbUpR06qDX885TpOpCIQET1Ul-0i2z-Wzc853CHlpeaKLyEqwNA4XlCxLwyyWcWhTpaJSJzlPsXZ4OJKD0-TDZ9FmE2ItTMMP0T24oWV4f40Gjg_S-1esoUVdF56DE-tL0-tkG9t6I33-wbhjkJKA0H2BUSqTUEjOWt7GKN7fnL8Rl7Zxiy9_BzpvkN0VGHrlK582Aa2PSP1bJG_X0iSinO8tF_le8eMXmsf_WuxtcnONV-m7RsHukGuuukt2em2buHvEjMFbrrAAi46nX6aWHmCpODjQt_TQ01NAVHtDJ3B8DlnJfQognXyvAHjW05rOSoqpJvST76JHj-rZV3c5ta4Tc5-c9g9PeoNw3bUhLBK474aiyDjjrLAlHHyiuOUuUQoMnWkhlLPMwY1GKl3qIs0iXgDk0y61TJQaBivFH5Ctala5R4RGzgkhdQqYsUycRHmZFVHJUutynbOAhO2ZmWJNaY6dNS5MQ8YcG9w2021bQF534781ZB5_HPnKq0A3LJufYwqcEuZs9N5oqfpD8EjmLCC01REDG49fW7LKzZa1gSiiAbslKiAPG93phMUx0rbJOCD8SplMhc2jaoN832uVMKvl3FQX-AMSapNgz16YFXtV-csSTG8y6XX_Hv_LpBdkZ3AyPDbHR6OPT8iuf05nccjkU7K1mC_dM8Bji_y5t7ifcBQrow |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1bb9MwFLZgk2A8cL-Eqx8QvJAtjm8xb6hd2YBVU8u0vVmJ7UC1KZ2aVh38eo6dJqMIhARPUaLjI_n43Oz4fAehl5YyZRIrwNIobFDyPIvzVKSxzaRMSsUKmvna4YOh2DtiH074yU9V_A0-RHfg5i0j-Gtv4Oe23LkEDTV1bQIEpy8vza6iTSYS5Zs39EcdgBR8CX8rSSZYzAUlLWxjku6sj18LS5tewhe_yzlvoK0l2HkVCp_W89kQkAa3UN5OpbmHcrq9mBfb5vsvKI__M9fb6OYqW8XvGvW6g6646i663mubxN1DegS-cunLr_Bo8mVicd8XioP7fIt3AzgFxLQ3eAyL5zwmebgAiMffKkg760mNpyX2F03wYeihh_fr6Vd3MbGuY3MfHQ12P_f24lXPhtgw2O3G3OSUUGJsCcvOJLXUMSnBzIniXDpLHOxnhFSlMlmeUAMJn3KZJbxUQCwlfYA2qmnlHiGcOMe5UBlkjCVzwvPLLU9KkllXqIJEKG6XTJsVoLnvq3GmGyjmVHux6U5sEXrd0Z83UB5_pHwVNKAjy2en_gKc5Pp4-F4rIQcH4I_0cYRwqyIaBO__teSVmy5qDTFEQebGZIQeNqrTMUtTD9om0gjRS13SlW8dVWuP9r3SCL1czHR15h_AodbMd-yFUWnQlL9MQffG41739vhfBr1A1w77A_1pf_jxCdoKZ-kkjYl4ijbms4V7BsnYvHge7O0HxxYqUg |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Renewable+rigid+diamines%3A+efficient%2C+stereospecific+synthesis+of+high+purity+isohexide+diamines&rft.jtitle=ChemSusChem&rft.au=Thiyagarajan%2C+Shanmugam&rft.au=Gootjes%2C+Linda&rft.au=Vogelzang%2C+Willem&rft.au=van+Haveren%2C+Jacco&rft.date=2011-12-16&rft.issn=1864-564X&rft.eissn=1864-564X&rft.volume=4&rft.issue=12&rft.spage=1823&rft_id=info:doi/10.1002%2Fcssc.201100398&rft.externalDBID=NO_FULL_TEXT |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1864-5631&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1864-5631&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1864-5631&client=summon |