CHEMISTRY OF HYPERVALENT SULFUR .9. BOND SWITCH WITH PARTICIPATION OF PI-BONDED SIV IN A THIADIAZOLE RING-SYSTEM

被引：44

作者：

AKIBA, K

KOBAYASHI, T

ARAI, S

机构：

[1] Department of Chemistry, University of Pennsylvania, Philadelphia

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 19期

关键词：

D O I：

10.1021/ja00513a081

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

It has been reported that π-hypervalent sulfur plays an important role in effecting cycloaddition of iminothiazolines to activated acetylenes,2 nitriles,3 isothiocyanates,4 and alsoin similar reactions involving 1,2-dithiole-3-thiones.5 We recently reported a unique example of rapid equilibrium due to acid-catalyzed bond switch at π-hypervalent sulfur.6 We now describe a ring-transformation equilibrium of the 1,2,4-thiadizole ring in neutral solution which can be understood as due to bond switch at π-hypervalent sulfur. © 1979, American Chemical Society. All rights reserved.

引用

页码：5857 / 5858

页数：2

共 12 条

[1] BOND SWITCH WITH PARTICIPATION OF PI-BONDED SIV IN THIATHIOPHTHENE-ANALOGOUS SYSTEMS
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[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (02): : 166 - 167
[2] AKIBA K, 1976, TETRAHEDRON LETT, P1877
[3] AKIBA KY, 1975, TETRAHEDRON LETT, P459
[4] AKIBA KY, 1975, TETRAHEDRON LETT, P455
[5] CYCLOADDITION OF DIMETHYL ACETYLENEDICARBOXYLATE WITH 2-IMINO-1,3-OXATHIOLES
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[7] DEROCQUE JL, 1968, B SOC CHIM FR, P2062
[8] N-CYANOIMIDATES
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[9] 4-ALKYL-5-(ARYLIMINO)-1,2,3,4-THIATRIAZOLINES AS MASKED 1,3-DIPOLES
LABBE, G
TIMMERMAN, A
MARTENS, C
TOPPET, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (26) : 4951 - 4955
[10] IMINO-1,2,4-DITHIAZOLES .1. ALKYLATION
OLIVER, JE
DEMILO, AB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (15) : 2225 - 2228

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