The Journal of Organic Chemistry

Selective transformation of O-2-(trimethylsilyl) ethyl and O-tert-butyl carbamates into O-benzyl carbamates using benzyl trichloroacetimidate

AGM Barrett, D Pilipauskas

Index: Barrett, Anthony G. M.; Pilipauskas, Daniel Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 5170 - 5173

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Citation Number: 19

Abstract

I tively, when R2 is a 2-(trimethylsily1) ethyl group, SN1 fragmentation and subsequent nucleophilic attack at sil-icon by the trichloroacetamide gives the product carbamate, ethylene, and the positively charged TMS adduct. However, when R2 is a methyl group, cleavage of the cation occurs presumably via debenzylation with the formation of N- benzyltrichloroacetamide rather than de-0-methylation with formation of the benzyl ...