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Diisobutylaluminum hydride a novel reagent for the reduction of oximes

✍ Scribed by Satoru Sasatani; Tohru Miyazaki; Keiji Maruoka; Hisashi Yamamoto

Book ID: 104220082
Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 131 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)86234-6

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✦ Synopsis

A simple procedure for converting oximes to rearranged secondary amines is described.

Although the direct transformation of oximes to rearranged secondary amines is an important synthetic operation, it has never been developed to a useful level due to the lack of a satisfactory reagent for selectivity.

For example, the lithium aluminum hydride (LAH) reduction of oximes is known to produce the corresponding primary amines, isomeric secondary amines, and aziridines depending on the nature of oxime substrates and the reduction conditions. l-3 During an investigation into the chemistry of tandem Beckmann rearrangement-alkylation sequence, 4 we have found a simple and highly convenient procedure for obtaining secondary amines exclusively from oximes5 by the use of diisobutylaluminum hydride (DIBAH) (eq 1).

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