The Chemistry of N,N-Bis(siloxy)enamines, Part 9. [1] A General Method for the Preparation of α-Hydroxy Oximes from Aliphatic Nitro Compounds

Abstract

A new convenient procedure for the preparation of a variety of α-hydroxy oximes from available aliphatic nitro compounds via intermediate N,N-bis(siloxy)enamines is presented. The mechanism of the key step, the rearrangement of N,N-bis(siloxy)en­amines, is discussed.

Key words

aliphatic nitro compounds - N,N-bis(siloxy)enamines - α-hydroxy oximes - rearrangement - silylation

References

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18

Our attempts to realize the transformation ANC → 4 as a one-step process (without isolation of BENA) failed because of the conditions needed for steps ANC → 1 and 1 → 4 differ considerably.

21

Attempts to selectively desilylate oximino group in derivatives 4a-i by use of small quantities of MeOH were unsuccessful because the desilylation of both functional groups proceeded with comparable rates.