The Journal of Organic Chemistry

Nitro displacement by methanethiol anion. Synthesis of bis-, tris-, pentakis-, and hexakis (methylthio) benzenes

JR Beck, JA Yahner

Index: Beck,J.R.; Yahner,J.A. Journal of Organic Chemistry, 1978 , vol. 43, # 10 p. 2048 - 2052

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Citation Number: 30

Abstract

4 5 thioether 2 (67% yield). When 2 was allowed to react with excess methanethiol anion (lithium salt) in cold DMF (ice bath) for 1 h, the product obtained was 3, 4, 5-tris (methylthi0) benzotrifluoride (3, 95%). Similar treatment of 1 yielded 3 directly (74%). The same reaction with 2-chloro-3, 5-dinitrobenzotrifluoride (4) 8 gave 2, 3, 5-tris (methylthio) benzotrifluoride (5, 7090). The bis thioether 6a (61%) could be obtained