Ketoximes to N-substituted thioamides via PSCl3 mediated Beckmann rearrangement

…, LK Pandey, S Mathur, MVS Suryanarayana

Index: Pathak, Uma; Pandey, Lokesh Kumar; Mathur, Sweta; Suryanarayana Chemical Communications, 2009 , # 36 p. 5409 - 5411

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Citation Number: 9

Abstract

On the basis of the BR mechanism, the selection rationale is interpreted as follows: PSCl 3 will react with oxime to form the intermediate ester I and HCl (Scheme 1). HCl shall in turn hydrolyse the intermediate ester I to form nitrilium ion II and chlorothiophosphoric acid. Further attack by chlorothiophosphoric acid on II followed by hydrolysis may ultimately yield the thioamide. To investigate the feasibility of this reaction acetophenone oxime was selected as a model ...