Stereoselective ring opening reaction of 2-[(phenylthio) methyl] cycloalkanols mediated by N-chlorosuccinimide and triethylamine

…, M Yasumura, T Tamura, K Negoro

Index: Takaki, Ken; Yasumura, Masateru; Tamura, Takao; Negoro, Kenji Journal of Organic Chemistry, 1987 , vol. 52, # 7 p. 1256 - 1261

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Citation Number: 2

Abstract

Treatment of 2-[l-(phenylthio) benzyl] cyclohexanol (2~) with N-chlorosuccinimide (NCS) and triethylamine gave various producta 3-6c depending on reaction conditions. Exclusive ring- opening reation of 2c was achieved by temperature control. Thus, five-, six-, and seven- membered cycloalkanols 2a-g were converted to W-OXO-a, p-unsaturated sulfides 6a-g in good yields. The stereochemistry of the reaction was determined by using four ...