Conformation and stereodynamics of alkyl 9-anthryl sulfoxides

被引：11

作者：

Jennings, WB ^{[1
]}

Kochanewycz, MJ ^{[1
]}

Lunazzi, L ^{[1
]}

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM ORGAN A MANGINI,I-40136 BOLOGNA,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1997年 / 11期

关键词：

D O I：

10.1039/a703184j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several alkyl 9-anthryl sulfoxides exhibit broadening of the aromatic peri-proton signal in H-1 NMR spectra recorded at ambient temperature due to hindered rotation about the 9-anthryl-sulfur bond; the rotational barriers lie in the range 10.9-18.9 kcal mol(-1). The preferred conformation and torsional barriers in these sulfoxides and in mesityl methyl sulfoxide have also been investigated by molecular mechanics calculations.

引用

页码：2271 / 2273

页数：3

共 9 条

[1] RESTRICTED ROTATION IN HINDERED ARYL METHYL SULFOXIDES AS DETECTED BY LOW-TEMPERATURE PROTON MAGNETIC-RESONANCE [J].

BUCHANAN, GW ;

REYESZAMORA, C ;

CHEUNG, C .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (17) :2537-2539

[2] DYNAMIC NUCLEAR MAGNETIC-RESONANCE INVESTIGATION OF PHOSPHONAMIDOTHIOIC AND PHOSPHONAMIDOUS CHLORIDES [J].

BURDON, J ;

HOTCHKISS, JC ;

JENNINGS, WB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (09) :1052-1058

[3] ATROPISOMERISM IN HINDERED NAPHTHYL SULFOXIDES - STRUCTURE, STEREODYNAMICS, AND CHIRAL RESOLUTION [J].

CASARINI, D ;

FORESTI, E ;

GASPARRINI, F ;

LUNAZZI, L ;

MACCIANTELLI, D ;

MISITI, D ;

VILLANI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5674-5682

[4] FREE RADICAL SUBSTITUTION IN 3,4-BENZPYRENE [J].

CONWAY, W ;

TARBELL, DS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (10) :2228-2233

[5] CHEMISTRY OF OXAZIRIDINES .8. ASYMMETRIC OXIDATION OF NONFUNCTIONALIZED SULFIDES TO SULFOXIDES WITH HIGH ENANTIOSELECTIVITY BY 2-SULFAMYLOXAZIRIDINES - THE INFLUENCE OF THE OXAZIRIDINE C-ARYL GROUP ON THE ASYMMETRIC INDUCTION [J].

DAVIS, FA ;

MCCAULEY, JP ;

CHATTOPADHYAY, S ;

HARAKAL, ME ;

TOWSON, JC ;

WATSON, WH ;

TAVANAIEPOUR, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3370-3377

[6]

FRIEDLANDER P, 1922, CHEM BER, V55, P3792

[7] THE PALLADIUM CATALYZED NUCLEOPHILIC-SUBSTITUTION OF ARYL HALIDES BY THIOLATE ANIONS [J].

MIGITA, T ;

SHIMIZU, T ;

ASAMI, Y ;

SHIOBARA, J ;

KATO, Y ;

KOSUGI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (05) :1385-1389

[8]

Oki M., 1985, APPL DYNAMIC NMR SPE

[9]

TAMANO M, 1984, NIPPON KAGAKU KAISHI, V7, P1158

← 1 →