GENERAL REGIOSPECIFIC SYNTHESIS OF ANNULATED QUINONES
A general regiospecific synthesis of annulated hydroquinones/quinones is presented. This specifically involves the thermal rearrangement of the 4-aryl-4-hydroxycyclobutenones 1a-k to the corresponding annulated hydroquinones. The synthetic scope and mechanism of this rearrangement are discussed.
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| Published in | Journal of organic chemistry Vol. 53; no. 5; pp. 996 - 1003 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
Amer Chemical Soc
04.03.1988
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| Subjects | |
| Online Access | Get full text |
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| Abstract | A general regiospecific synthesis of annulated hydroquinones/quinones is presented. This specifically involves the thermal rearrangement of the 4-aryl-4-hydroxycyclobutenones 1a-k to the corresponding annulated hydroquinones. The synthetic scope and mechanism of this rearrangement are discussed. |
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| AbstractList | A general regiospecific synthesis of annulated hydroquinones/quinones is presented. This specifically involves the thermal rearrangement of the 4-aryl-4-hydroxycyclobutenones 1a-k to the corresponding annulated hydroquinones. The synthetic scope and mechanism of this rearrangement are discussed. |
| Author | PERRI, ST MOORE, HW |
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| DOI | 10.1021/jo00240a011 |
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| References | PERRI, ST (WOS:A1986D406300045) 1986; 51 SPANGLER, LA (WOS:A1984SS68200026) 1984; 49 SHIRLEY, DA (WOS:A1968A619900007) 1968; 11 LIEBESKIND, LS (WOS:A1986D406300044) 1986; 51 KRAUS, JL (WOS:A1985AFA6300022) 1985; 26 SWENTON, JS (WOS:A1978FP28200038) 1978; 100 DOTZ, KH (WOS:A1978FJ35200005) 1978; 111 RANDAN NG (WOS:A1988M371900011.25) 1985; 107 COHEN, S (WOS:A19667534100040) 1966; 88 KARLSSON, JO (WOS:A1985AJD7800081) 1985; 107 FISHER A (WOS:A1988M371900011.9) 1985 CURRY, MJ (WOS:A1980KN30600002) 1980 MURTHY DVK (WOS:A1988M371900011.21) 1985; 44 SPANGLER, LA (WOS:A1986C868500008) 1986 HUISGEN, R (WOS:A1976BD52200021) 1976 DANHEISER, RL (WOS:A1984SP90300043) 1984; 49 ARNOLD, BJ (WOS:A1974S570400018) 1974 NIEUWENHUIS, J (WOS:A1958WT03400021) 1958; 77 DOTZ, KH (WOS:A1983RT05600003) 1983; 55 SMITH LI (WOS:A1988M371900011.28) 1941; 63 ARNOLD, BJ (WOS:A1974S570400019) 1974 MAYR, H (WOS:A1976BD52200022) 1976 SMITH LI (WOS:A1988M371900011.29) 1939; 61 KIRMSE, W (WOS:A1984TW47400067) 1984; 106 JONES, GH (WOS:A1986D452700031) 1986; 29 NEUSE, EW (WOS:A1974U416300016) 1974 SCHMIDT, AH (WOS:A1980KV18600001) 1980 FLYNN, DL (WOS:A1986E469400008) 1986; 27 DOLBIER, WR (WOS:A1984SJ28800071) 1984; 106 Hurd, CDW (WOS:000188447900076) 1925; 47 ZUBOVICS, Z (WOS:A1972O460900003) 1972; 765 WITTMANN, H (WOS:A1968C077400043) 1968; 99 KIPPING, C (WOS:A1973R406700010) 1973; 315 MAYR, H (WOS:A1975AL11700019) 1975; 14 |
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THERMAL GENERATION OF PHOTOENOLS AND THEIR DERIVATIVES FROM DISUBSTITUTED 1,2-DIHYDROBENZOCYCLOBUTENES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: ARNOLD, BJ – volume: 99 start-page: 1982 year: 1968 ident: WOS:A1968C077400043 article-title: SYNTHESIS OF HETEROCYCLES .115. KETENES FROM MIXED ANHYDRIDES OF PHENYLMALONIC ACID publication-title: MONATSHEFTE FUR CHEMIE contributor: fullname: WITTMANN, H – volume: 11 start-page: 209 year: 1968 ident: WOS:A1968A619900007 article-title: PRODUCT DISTRIBUTION IN METALATION OF SOME AROMATIC SUBSTRATES WITH N-BUTYLLITHIUM publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: SHIRLEY, DA – volume: 106 start-page: 1871 year: 1984 ident: WOS:A1984SJ28800071 article-title: REMARKABLE, CONTRASTERIC, ELECTROCYCLIC RING-OPENING OF A CYCLOBUTENE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: DOLBIER, WR – start-page: 961 year: 1980 ident: WOS:A1980KV18600001 article-title: REACTIONS OF QUADRATIC ACID AND ITS DERIVATIVES publication-title: SYNTHESIS-STUTTGART contributor: fullname: SCHMIDT, AH – volume: 107 start-page: 3392 year: 1985 ident: WOS:A1985AJD7800081 article-title: (2-ALKYNYLETHENYL)KETENES - A NEW BENZOQUINONE SYNTHESIS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: KARLSSON, JO – volume: 49 start-page: 1800 year: 1984 ident: WOS:A1984SS68200026 article-title: MECHANISTIC ASPECTS OF THE ANNELATION REACTIONS OF BENZOCYCLOBUTENEDIONE MONOKETALS WITH VINYLLITHIUM REAGENTS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: SPANGLER, LA – start-page: 55 year: 1976 ident: WOS:A1976BD52200021 article-title: REACTIONS OF CYCLOBUTENONES WITH NUCLEOPHILIC-REAGENTS VIA VINYLKETEN INTERMEDIATES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: HUISGEN, R – start-page: 1391 year: 1980 ident: WOS:A1980KN30600002 article-title: THE THERMAL RING-OPENING OF 3,3-DISUBSTITUTED CYCLOBUTENES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 contributor: fullname: CURRY, MJ – volume: 26 start-page: 1867 year: 1985 ident: WOS:A1985AFA6300022 article-title: REACTIVITY OF ORGANO LITHIUM REAGENTS ON DIMETHYL SQUARATE - A 1,2-ADDITION PROCESS LEADING TO NEW 2-HYDROXY-3,4 DIMETHOXY 3-CYCLOBUTENONE publication-title: TETRAHEDRON LETTERS contributor: fullname: KRAUS, JL – start-page: 409 year: 1974 ident: WOS:A1974S570400018 article-title: PHOTOCHEMICAL REACTIONS .3. 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TEMPLATE REACTIONS ON CHROMIUM(O) - STEREOSELECTIVE SYNTHESIS OF CONDENSED AROMATIC LIGANDS FROM PENTACARBONYL(CARBENE)CHROMIUM COMPLEXES AND ALKYNES publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: DOTZ, KH – volume: 88 start-page: 1533 year: 1966 ident: WOS:A19667534100040 article-title: PREPARATION AND REACTIONS OF DERIVATIVES OF SQUARIC ACID . 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| Title | GENERAL REGIOSPECIFIC SYNTHESIS OF ANNULATED QUINONES |
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