C-13 NUCLEAR MAGNETIC-RESONANCE STUDY OF BENZO[B]THIOPHENES AND BENZO[B]THIOPHENE S-OXIDES AND S,S,-DIOXIDES

被引:35
作者
GENESTE, P [1 ]
OLIVE, JL [1 ]
UNG, SN [1 ]
ELAMOUDIELFAGHI, M [1 ]
EASTON, JW [1 ]
BIERBECK, H [1 ]
SAUNDERS, JK [1 ]
机构
[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SHERBROOKE J1K 2R1,QUEBEC,CANADA
关键词
D O I
10.1021/jo01330a013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 13C NMR spectra of benzo[b]thiophenes and a series of benzo[b]thiophene S-oxides and S, S-dioxides of well-defined structure were recorded. A comparison between benzothiophenes and the sulfoxide and sulfone derivatives permits the characterization of the effect of the sulfoxide and sulfone moieties on 13C chemical shifts in this heteroaromatic system. A comparison of the 13C resonances of benzothiophene S-oxides and S, S-dioxides with the corresponding derivatives of 2, 3-dihydrobenzothiophene shows a decrease in aromaticity on going from the benzo[b] thiophene to the S-oxide and S, S-dioxide systems, the sulfoxide being more aromatic than the sulfone. © 1979, American Chemical Society. All rights reserved.
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页码:2887 / 2892
页数:6
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