Nitrosation of oxime

The nitrosation of oximes can also serve to produce N-hydroxy-N-nitrosamines (Scheme 3.9). The acidified nitrite procedure can be applied to oximes derived from terpenes [132] and hydroxyguanidine [133] for the synthesis of N-hydroxy-N-nitrosamines. However, some a, 5-uri saturated oximes were converted into pyrazole-1,2-dioxides [134]. The alkyl nitrites under basic conditions have produced interesting results. Quinone dioximes yielded only monodiazeniumdiolates [135], while simple aliphatic oximes gave products resulting from addition to the imine double bond... 

N-Nitrosation of oximes by nitrosyl halides or nitrite esters often results in the formation of N-nitrimines, R R C=NN02, these compounds being formed by rearrangement of the initial adducts. N-Amination of oximes by chloramine or by hydroxylamine-O-sulfonic acid can result in the formation of diazo compounds (Scheme 28). The reaction, known as the Forster reaction, has been used for the preparation of aryldiazoalkanes, although better methods are usually available. Diazo ketones of the general formula (49) have also been prepared by this method from the oximes. "... 

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