The Journal of Organic Chemistry

Thermal rearrangement of O-(2, 4, 6-trihalophenyl) N, N-dimethylthiocarbamates. An abnormal pathway

CE Reineke, CT Goralski

Index: Reinecke,C.E.; Goralski,C.T. Journal of Organic Chemistry, 1977 , vol. 42, # 7 p. 1139 - 1142

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Citation Number: 9

Abstract

The conversion of phenols to benzenethiols via the N, N-dimethylthiocarbamates has been applied to the 2, 4, 6-trihalophenols. Results were highly dependent on whether the halogen was C1, Br, or I. The pyrolysis of 0-(2, 4, 6-trichlorophenyl) N, N-dimethylthiocarbamate (1) yielded S-(2, 4, 6-trichlorophenyl) N, N-dimethylthiocarbamate (2) which on hydrolysis gave 2, 4, 6-trichlorobenzenethiol (3). The pyrolysis of 0-(2, 4, 6-tribromophenyl) N, N- ...