Tetrahedron letters

Reaction of 2, 5-dimethylene-2, 5-dihydrothiophene with triplet oxygen

CS Huang, CC Peng, CH Chou

Index: Huang, Chin-Shui; Peng, Chun-Chieh; Chou, Chin-Hsing Tetrahedron Letters, 1994 , vol. 35, # 24 p. 4175 - 4176

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Citation Number: 12

Abstract

Abstract 2, 5-Dimethylene-2, 5-dihydrothiophene (1), prepared by the pyrolysis of 5- methylthenyl benzoate (3), has been detected by low-temperature NMR spectroscopy. 1 reacts with triplet oxygen to form a cyclic bisperoxide 6. Upon heating, 6 decomposes to give 2, 5-bis (hydroxymethyl) thiophene (7), 2-formyl-5-hydroxymethylthiophene (8) and 2, 5- diformylthiophene (9) in a ratio of 1: 2: 1, respectively.

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