SULFUR-BRIDGED CARBOCYCLES .3. PHOTOCYCLIZATION OF BETA BETA'-DIPHENYLDIVINYL SULFIDE

被引：33

作者：

BLOCK, E

COREY, EJ

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 04期

关键词：

D O I：

10.1021/jo01256a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

β,β′-Diphenyldivinyl sulfide (2a) has been found to undergo facile cyclization on irradiation to trans-2,3- diphenyl-5-thiabicyclo[2.1.0]pentane (3a), the first known example of a cyclobutene episulfide. Bicyclic sulfide 3a undergoes desulfurization with trivalent organophosphorus compounds giving trans,trans-1,4-diphenylbutadiene, presumably by way of thermally unstable trans-3,4-diphenylcyclobutene (9). A second product of the irradiation of sulfide 2a has been identified as 2,3-dihydro-3,4-diphenylthiophene (10). © 1969, American Chemical Society. All rights reserved.

引用

页码：896 / &

共 32 条

[1]

BATTISTE MA, 1966, TETRAHEDRON LETT, P523

[2]

BLOCK E, 1967, THESIS HARVARD U

[3]

Bothner-By A.A., 1965, ADV MAGNETIC OPTICAL, VVolume 1, P195

[4] NATURE OF SULFUR BONDING IN ALPHA,BETA-UNSATURATED SULFIDES AND SULFONIUM SALTS [J].