Substituent effects on the ring-chain tautomerism of some 1,3-oxazolidine derivatives
The 14 and 70 eV electron ionization mass spectra of five sets (R1 = Me, Et, i‐Pr, t‐Bu and Ph) of seven 2‐aryl‐4‐R1‐substituted (Ar = C6H4X; X = p‐NO2, m‐Br, p‐Cl, H, p‐Me, p‐OMe and p‐NMe2) (1–5) and of seven 2‐aryl‐5‐phenyl‐substituted 1,3‐oxazolidines (6; for Ar, see above) were recorded to stud...
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| Published in | Rapid communications in mass spectrometry Vol. 22; no. 10; pp. 1510 - 1518 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Chichester, UK
John Wiley & Sons, Ltd
30.05.2008
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| Abstract | The 14 and 70 eV electron ionization mass spectra of five sets (R1 = Me, Et, i‐Pr, t‐Bu and Ph) of seven 2‐aryl‐4‐R1‐substituted (Ar = C6H4X; X = p‐NO2, m‐Br, p‐Cl, H, p‐Me, p‐OMe and p‐NMe2) (1–5) and of seven 2‐aryl‐5‐phenyl‐substituted 1,3‐oxazolidines (6; for Ar, see above) were recorded to study their ring‐chain equilibria in the gas phase. These equilibria were also studied by 1H NMR spectroscopy in CDCl3 for compounds 5 and 6. A few 2,4‐ and 2,5‐dimethyl‐2‐aryl derivatives (7, 8: Ar = C6H4X; X = m‐Br, H and p‐OMe) were studied both in CDCl3 and in the gas phase. The main characteristics of the ring‐chain equilibria expressed by the variable ΣRA% of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C‐2 and C‐4. The results in the gas phase are compared with those in CDCl3. Copyright © 2008 John Wiley & Sons, Ltd. |
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| AbstractList | The 14 and 70 eV electron ionization mass spectra of five sets (R1 = Me, Et, i-Pr, t-Bu and Ph) of seven 2-aryl-4-R1-substituted (Ar = C6H4X; X = p-NO2, m-Br, p-Cl, H, p-Me, p-OMe and p-NMe2) (1-5) and of seven 2-aryl-5-phenyl-substituted 1,3-oxazolidines (6; for Ar, see above) were recorded to study their ring-chain equilibria in the gas phase. These equilibria were also studied by 1H NMR spectroscopy in CDCl3 for compounds 5 and 6. A few 2,4- and 2,5-dimethyl-2-aryl derivatives (7, 8: Ar = C6H4X; X = m-Br, H and p-OMe) were studied both in CDCl3 and in the gas phase. The main characteristics of the ring-chain equilibria expressed by the variable SigmaRA% of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C-2 and C-4. The results in the gas phase are compared with those in CDCl3. The 14 and 70 eV electron ionization mass spectra of five sets (R 1 = Me, Et, i ‐Pr, t ‐Bu and Ph) of seven 2‐aryl‐4‐R 1 ‐substituted (Ar = C 6 H 4 X; X = p ‐NO 2 , m ‐Br, p ‐Cl, H, p ‐Me, p ‐OMe and p‐ NMe 2 ) (1–5) and of seven 2‐aryl‐5‐phenyl‐substituted 1,3‐oxazolidines (6; for Ar, see above) were recorded to study their ring‐chain equilibria in the gas phase. These equilibria were also studied by 1 H NMR spectroscopy in CDCl 3 for compounds 5 and 6. A few 2,4‐ and 2,5‐dimethyl‐2‐aryl derivatives (7, 8: Ar = C 6 H 4 X; X = m ‐Br, H and p ‐OMe) were studied both in CDCl 3 and in the gas phase. The main characteristics of the ring‐chain equilibria expressed by the variable Σ RA % of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C‐2 and C‐4. The results in the gas phase are compared with those in CDCl 3 . Copyright © 2008 John Wiley & Sons, Ltd. The 14 and 70eV electron ionization mass spectra of five sets (R1=Me, Et, i-Pr, t-Bu and Ph) of seven 2-aryl-4-R1-substituted (Ar=C6H4X; X=p-NO2, m-Br, p-Cl, H, p-Me, p-OMe and p-NMe2) (1-5) and of seven 2-aryl-5-phenyl-substituted 1,3-oxazolidines (6; for Ar, see above) were recorded to study their ring-chain equilibria in the gas phase. These equilibria were also studied by 1H NMR spectroscopy in CDCl3 for compounds 5 and 6. A few 2,4- and 2,5-dimethyl-2-aryl derivatives (7, 8: Ar=C6H4X; X=m-Br, H and p-OMe) were studied both in CDCl3 and in the gas phase. The main characteristics of the ring-chain equilibria expressed by the variable RA% of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C-2 and C-4. The results in the gas phase are compared with those in CDCl3. The 14 and 70 eV electron ionization mass spectra of five sets (R1 = Me, Et, i‐Pr, t‐Bu and Ph) of seven 2‐aryl‐4‐R1‐substituted (Ar = C6H4X; X = p‐NO2, m‐Br, p‐Cl, H, p‐Me, p‐OMe and p‐NMe2) (1–5) and of seven 2‐aryl‐5‐phenyl‐substituted 1,3‐oxazolidines (6; for Ar, see above) were recorded to study their ring‐chain equilibria in the gas phase. These equilibria were also studied by 1H NMR spectroscopy in CDCl3 for compounds 5 and 6. A few 2,4‐ and 2,5‐dimethyl‐2‐aryl derivatives (7, 8: Ar = C6H4X; X = m‐Br, H and p‐OMe) were studied both in CDCl3 and in the gas phase. The main characteristics of the ring‐chain equilibria expressed by the variable ΣRA% of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C‐2 and C‐4. The results in the gas phase are compared with those in CDCl3. Copyright © 2008 John Wiley & Sons, Ltd. The 14 and 70 eV electron ionization mass spectra of five sets (R1 = Me, Et, i-Pr, t-Bu and Ph) of seven 2-aryl-4-R1-substituted (Ar = C6H4X; X = p-NO2, m-Br, p-Cl, H, p-Me, p-OMe and p-NMe2) (1-5) and of seven 2-aryl-5-phenyl-substituted 1,3-oxazolidines (6; for Ar, see above) were recorded to study their ring-chain equilibria in the gas phase. These equilibria were also studied by 1H NMR spectroscopy in CDCl3 for compounds 5 and 6. A few 2,4- and 2,5-dimethyl-2-aryl derivatives (7, 8: Ar = C6H4X; X = m-Br, H and p-OMe) were studied both in CDCl3 and in the gas phase. The main characteristics of the ring-chain equilibria expressed by the variable SigmaRA% of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C-2 and C-4. The results in the gas phase are compared with those in CDCl3.The 14 and 70 eV electron ionization mass spectra of five sets (R1 = Me, Et, i-Pr, t-Bu and Ph) of seven 2-aryl-4-R1-substituted (Ar = C6H4X; X = p-NO2, m-Br, p-Cl, H, p-Me, p-OMe and p-NMe2) (1-5) and of seven 2-aryl-5-phenyl-substituted 1,3-oxazolidines (6; for Ar, see above) were recorded to study their ring-chain equilibria in the gas phase. These equilibria were also studied by 1H NMR spectroscopy in CDCl3 for compounds 5 and 6. A few 2,4- and 2,5-dimethyl-2-aryl derivatives (7, 8: Ar = C6H4X; X = m-Br, H and p-OMe) were studied both in CDCl3 and in the gas phase. The main characteristics of the ring-chain equilibria expressed by the variable SigmaRA% of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C-2 and C-4. The results in the gas phase are compared with those in CDCl3. |
| Author | Juhász, Márta Pihlaja, Kalevi Kivelä, Henri Fülöp, Ferenc |
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| Cites_doi | 10.1016/S0040-4020(01)81538-6 10.1002/jhet.5570440635 10.3891/acta.chem.scand.45-0273 10.1007/BF02256908 10.1007/BF02253222 10.1002/(SICI)1097-0231(19980715)12:13<876::AID-RCM247>3.0.CO;2-0 10.1016/S0040-4020(98)00840-0 10.3987/COM-93-S121 10.1002/oms.1210291112 10.1002/rcm.3260 10.1002/oms.1210260512 10.1016/S0040-4020(01)98154-2 10.1002/oms.1210240510 |
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| References | Juhász M, Fülöp F, Pihlaja K. Rapid Commun. Mass Spectrom. 2007; 21: 3701. Vainiotalo P, Fülöp F, Pihlaja K. Org. Mass Spectrom. 1991; 26: 438. Vainiotalo P, Ronkanen S, Fülöp F, Pihlaja K. Tetrahedron 1990; 46: 3683. Fülöp F, Dahlqvist M, Pihlaja K. Acta Chem. Scand. 1991; 45: 273. Splitter JS, Tureček F. Applications of Mass Spectrometry to Organic Stereochemistry. VCH: New York, 1994. Terent'ev PB, Kalandarishvili AG, Zelenin KN, Solod OV, Shevtsov VK. Chem. Heterocycl. Compds. 1997; 33: 1070. Lázár L, Göblyös A, Evanics F, Bernáth G, Fülöp F. Tetrahedron 1998; 54: 13639. Vainotalo P, Ronkanen S, Lehtelä PL, Smolander R, Fülöp F, Pihlaja K. Saturated Heterocycles (in the series A Magyar Tudományos Akadémia Szegedi Területi Bizottsága Kiadványai) 1993; 3: 87. Juhász M, Lázár L, Fülöp F. J. Heterocycl. Chem. 2007; 44: 1465. Walker RB, Moore DS, Massey MD. Org. Mass Spectrom. 1989; 24: 345. Joutsiniemi K, Vainiotalo P, Fülöp F, Lázár L. Rapid Commun. Mass Spectrom. 1998; 12: 876. Rennekamp ME, Paukstelis JV, Cooks RG. Tetrahedron 1971; 27: 4407. Lehtelä PL, Smolander R, Vainiotalo P. Org. Mass Spectrom. 1994; 29: 647. Fülöp F, Sillanpää R, Dahlqvist M, Pihlaja K, Vainiotalo P. Heterocycles 1994; 37: 1093. Lebedev A, Leite L, Fleisher M, Stonkus V. Chem. Heterocycl. Compds. 2000; 36: 775. 1990; 46 1991; 26 1997; 33 2000; 36 1991; 45 1971; 27 1986 1994 1994; 37 1994; 29 2007; 21 2007; 44 1989; 24 1998; 54 1993; 3 1998; 12 e_1_2_7_5_2 Vainotalo P (e_1_2_7_12_2) 1993; 3 e_1_2_7_4_2 e_1_2_7_2_2 e_1_2_7_9_2 e_1_2_7_8_2 e_1_2_7_7_2 e_1_2_7_6_2 e_1_2_7_18_2 e_1_2_7_17_2 e_1_2_7_16_2 e_1_2_7_15_2 e_1_2_7_14_2 e_1_2_7_13_2 e_1_2_7_11_2 e_1_2_7_10_2 Splitter JS (e_1_2_7_3_2) 1994 |
| References_xml | – reference: Walker RB, Moore DS, Massey MD. Org. Mass Spectrom. 1989; 24: 345. – reference: Rennekamp ME, Paukstelis JV, Cooks RG. Tetrahedron 1971; 27: 4407. – reference: Splitter JS, Tureček F. Applications of Mass Spectrometry to Organic Stereochemistry. VCH: New York, 1994. – reference: Vainiotalo P, Fülöp F, Pihlaja K. Org. Mass Spectrom. 1991; 26: 438. – reference: Fülöp F, Sillanpää R, Dahlqvist M, Pihlaja K, Vainiotalo P. Heterocycles 1994; 37: 1093. – reference: Fülöp F, Dahlqvist M, Pihlaja K. Acta Chem. Scand. 1991; 45: 273. – reference: Terent'ev PB, Kalandarishvili AG, Zelenin KN, Solod OV, Shevtsov VK. Chem. Heterocycl. Compds. 1997; 33: 1070. – reference: Vainotalo P, Ronkanen S, Lehtelä PL, Smolander R, Fülöp F, Pihlaja K. Saturated Heterocycles (in the series A Magyar Tudományos Akadémia Szegedi Területi Bizottsága Kiadványai) 1993; 3: 87. – reference: Lebedev A, Leite L, Fleisher M, Stonkus V. Chem. Heterocycl. Compds. 2000; 36: 775. – reference: Juhász M, Lázár L, Fülöp F. J. Heterocycl. Chem. 2007; 44: 1465. – reference: Juhász M, Fülöp F, Pihlaja K. Rapid Commun. Mass Spectrom. 2007; 21: 3701. – reference: Vainiotalo P, Ronkanen S, Fülöp F, Pihlaja K. Tetrahedron 1990; 46: 3683. – reference: Joutsiniemi K, Vainiotalo P, Fülöp F, Lázár L. Rapid Commun. Mass Spectrom. 1998; 12: 876. – reference: Lehtelä PL, Smolander R, Vainiotalo P. Org. Mass Spectrom. 1994; 29: 647. – reference: Lázár L, Göblyös A, Evanics F, Bernáth G, Fülöp F. Tetrahedron 1998; 54: 13639. – year: 1986 – volume: 26 start-page: 438 year: 1991 publication-title: Org. Mass Spectrom. – volume: 44 start-page: 1465 year: 2007 publication-title: J. Heterocycl. Chem. – volume: 36 start-page: 775 year: 2000 publication-title: Chem. Heterocycl. Compds. – volume: 45 start-page: 273 year: 1991 publication-title: Acta Chem. Scand. – volume: 37 start-page: 1093 year: 1994 publication-title: Heterocycles – volume: 21 start-page: 3701 year: 2007 publication-title: Rapid Commun. Mass Spectrom. – volume: 54 start-page: 13639 year: 1998 publication-title: Tetrahedron – volume: 27 start-page: 4407 year: 1971 publication-title: Tetrahedron – volume: 29 start-page: 647 year: 1994 publication-title: Org. Mass Spectrom. – volume: 46 start-page: 3683 year: 1990 publication-title: Tetrahedron – volume: 24 start-page: 345 year: 1989 publication-title: Org. Mass Spectrom. – year: 1994 – volume: 33 start-page: 1070 year: 1997 publication-title: Chem. Heterocycl. Compds. – volume: 12 start-page: 876 year: 1998 publication-title: Rapid Commun. Mass Spectrom. – volume: 3 start-page: 87 year: 1993 publication-title: Saturated Heterocycles (in the series A Magyar Tudományos Akadémia Szegedi Területi Bizottsága Kiadványai) – volume: 3 start-page: 87 year: 1993 ident: e_1_2_7_12_2 publication-title: Saturated Heterocycles (in the series A Magyar Tudományos Akadémia Szegedi Területi Bizottsága Kiadványai) – ident: e_1_2_7_6_2 doi: 10.1016/S0040-4020(01)81538-6 – ident: e_1_2_7_10_2 – ident: e_1_2_7_9_2 doi: 10.1002/jhet.5570440635 – ident: e_1_2_7_18_2 doi: 10.3891/acta.chem.scand.45-0273 – ident: e_1_2_7_8_2 doi: 10.1007/BF02256908 – ident: e_1_2_7_7_2 doi: 10.1007/BF02253222 – ident: e_1_2_7_11_2 – volume-title: Applications of Mass Spectrometry to Organic Stereochemistry year: 1994 ident: e_1_2_7_3_2 – ident: e_1_2_7_15_2 doi: 10.1002/(SICI)1097-0231(19980715)12:13<876::AID-RCM247>3.0.CO;2-0 – ident: e_1_2_7_16_2 doi: 10.1016/S0040-4020(98)00840-0 – ident: e_1_2_7_5_2 doi: 10.3987/COM-93-S121 – ident: e_1_2_7_13_2 doi: 10.1002/oms.1210291112 – ident: e_1_2_7_2_2 doi: 10.1002/rcm.3260 – ident: e_1_2_7_4_2 doi: 10.1002/oms.1210260512 – ident: e_1_2_7_17_2 doi: 10.1016/S0040-4020(01)98154-2 – ident: e_1_2_7_14_2 doi: 10.1002/oms.1210240510 |
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| Snippet | The 14 and 70 eV electron ionization mass spectra of five sets (R1 = Me, Et, i‐Pr, t‐Bu and Ph) of seven 2‐aryl‐4‐R1‐substituted (Ar = C6H4X; X = p‐NO2, m‐Br,... The 14 and 70 eV electron ionization mass spectra of five sets (R 1 = Me, Et, i ‐Pr, t ‐Bu and Ph) of seven 2‐aryl‐4‐R 1 ‐substituted (Ar = C 6 H 4 X; X = p... The 14 and 70 eV electron ionization mass spectra of five sets (R1 = Me, Et, i-Pr, t-Bu and Ph) of seven 2-aryl-4-R1-substituted (Ar = C6H4X; X = p-NO2, m-Br,... The 14 and 70eV electron ionization mass spectra of five sets (R1=Me, Et, i-Pr, t-Bu and Ph) of seven 2-aryl-4-R1-substituted (Ar=C6H4X; X=p-NO2, m-Br, p-Cl,... |
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| Title | Substituent effects on the ring-chain tautomerism of some 1,3-oxazolidine derivatives |
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