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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 6
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Original Articles

Alkyloximes and Imines via Silyl Carbamates

, , , &
Pages 914-924 | Received 06 Nov 2009, Published online: 25 Feb 2011
 

Abstract

The reactions between different N,O-bis-trimethylsilyl-carbamates and oxo compounds were studied. The N,O-bis-trimethylsilyl-N-methoxy-carbamate converts ketones to the corresponding O-methyl oximes. The product is usually a mixture of syn and anti isomers. If the carbonyl compound bears a hydroxyl group, the oxime formation and the O-silylation take place simultaneously. In the case of α-haloketones, the undesired substitution of halogen was not observed. The reactions between N,O-bis-trimethylsilyl-N-methyl-carbamate and oxo compounds resulted in the corresponding imines, although the yield are moderate in some cases. Analoguos reaction of ferrocenylated oxo derivatives gave similar results.

ACKNOWLEDGMENT

This work was supported by the Hungarian National Science Foundation (OTKA) Grant Nos. F030821 and T025830.

Notes

a Molar ratio of oxo compound and N,O-bis-trimethylsilyl-N-methyl-carbamate.

b Molar ratio of trifluoroacetic acid catalyst and oxo compound.

c With N,O-bis-trimethylsilyl-N-trimethylsiloxy-carbamate.

a Molar ratio of oxo compound and N,O-bis-trimethylsilyl-N-methyl-carbamate.

b Molar ratio of trifluoroacetic acid catalyst and oxo compound.

c Not isolated; even repeated distillation resulted in a mixture of the product and the starting ketone.

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