Oligomerization of the Thiophene-Based p-Quinodimethanes 2, 5-Dimethylene-2, 5-dihydrothiophene and 2-Ethylidene-5-methylene-2, 5-dihydrothiophene

WS Trahanovsky, DL Miller, Y Wang

Index: Trahanovsky, Walter S.; Miller, Deborah Louise; Wang, Yili Journal of Organic Chemistry, 1997 , vol. 62, # 26 p. 8980 - 8986

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Citation Number: 10

Abstract

Flash vacuum pyrolysis (FVP) of (5-methyl-2-thiophene-yl) methyl benzoate (8) produces in ca. 75% yield 2, 5-dimethylene-2, 3-dihydrothiophene, S-monomer (3). S-Monomer 3 is relatively stable dissolved in carbon disulfide-chloroform at-78° C. The structure of 3 is confirmed by its spectral properties. When a 0.17 M solution of S-monomer 3 was allowed to warm to room temperature, SS-dimer 5 ([2, 2](2, 5) thiophenophane, 14.7%), SSS-trimer 7 ...