Role of sulfur in Beckmann fragmentation
RK Hill, DA Cullison
Index: Hill,R.K.; Cullison,D.A. Journal of the American Chemical Society, 1973 , vol. 95, # 9 p. 2923 - 2927
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Citation Number: 14
Abstract
Abstract: Oximes of two cyclic@-keto sulfides, 2 and 9, have been shown capable of undergoing carbonium ion fragmentation under certain Beckmann conditions. These findings cast doubt on a mechanism earlier proposed in which sulfur effects nucleophilic displacement on nitrogen and support, instead, the normal fragmentation mechanism. ximes substituted at an a carbon by groups capable 0 of stabilizing a positive charge frequently ...
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