The Journal of organic chemistry

Ring opening of 2, 5-didehydrothiophene: Matrix photochemistry of C4H2S isomers

YS Kim, H Inui, RJ McMahon

Index: Kim, Yong Seol; Inui, Hiroshi; McMahon, Robert J. Journal of Organic Chemistry, 2006 , vol. 71, # 26 p. 9602 - 9608

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Citation Number: 3

Abstract

Irradiation (λ> 254 nm) of matrix-isolated 2, 5-diiodothiophene (10) gives rise to IR bands assigned to ethynylthioketene (6). Diethynyl sulfide (3), which would form in the process of retro-Bergman cyclization of the incipient 2, 5-didehydrothiophene (4), is not detected. Under the same irradiation conditions, matrix-isolated diethynyl sulfide (3) rearranges to thioketene 6 and butatrienethione (5), the global minimum on C4H2S potential energy ...