Generation and electrophilic reactions of the 2, 2, 2-trifluoro-1-(phenylthio) ethyl carbocation

K Uneyama, M Momota, K Hayashida…

Index: Uneyama, Kenji; Momota, Makoto; Hayashida, Kazuaki; Itoh, Toshiyuki Journal of Organic Chemistry, 1990 ,  vol. 55,  # 19  p. 5364 - 5368

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Citation Number: 34

Abstract

2, 2, 2-Trifluoro-l-(phenylthio) ethyl carbocation (4) has been generated by the reaction of l- chloro-2, 2, 2-trifluoroethyl phenyl sulfide (7b) with ZnC1, in nitromethane or SnCl, in 1, 2- dichloroethane. The carbocation 4 can be trapped with various aromatics bearing electron- donating groups, affording l-aryl-2, 2, 2-trifluoroethyl phenyl sulfide 2 in 37-83% yields. Similarly, allyltrimethylsilane and various nitriles provided the corresponding allylated ...