The Journal of Organic Chemistry

Synthesis and structure of a new stable carbocation stabilized by two neighboring sulfur atoms. Dimethyl [9, 9-bis (methylthio)-1-fluorenyl] carbenium ion

M Hojo, T Ichi, K Shibato

Index: Hojo, Masaru; Ichi, Tadaaki; Shibato, Kishio Journal of Organic Chemistry, 1985 , vol. 50, # 9 p. 1478 - 1482

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Citation Number: 17

Abstract

The HD exchange experiments confirm the assignments of the'H NMR signals at 6 2.70 and 1.95 (two nonequivalent C-methyls) and 2.31 (two equivalent S-methyls). This is based on the reasoning that in strong acid neither the SCH, nor the SfCH3 group undergoes HD exchange, whereas exchange is possible for the C+ CH3 group, probably via the olefin. This assignment was supported by 13C NMR data for enriched alcohol 2 (Table 111).