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

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[2] BLOCK E, 1967, THESIS HARVARD U
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[5] CYCLIC POLYOLEFINS .44. THE STRUCTURE OF CYCLOOCTATETRAENE OXIDE
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (20) : 5505 - 5507
[6] NEW SYNTHETIC APPROACHES TO SYMMETRICAL SULFUR-BRIDGED CARBOCYCLES
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BLOCK, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (06) : 1663 - &
[7] COREY EJ, IN PRESS
[8] COREY EJ, UNPUBLISHED FINDINGS
[9] CRIEGEE R, 1959, ANN, V627, P1
[10] DEGANI J, 1961, B SCI FAC CHIM IND B, V19, P50

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