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
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.
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页码:896 / &
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