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Reductive Beckmann fragmentation of α-alkoxycycloalkanone oxime acetates

✍ Scribed by Hiromichi Fujioka; Hideaki Yamamoto; Makoto Miyazaki; Takeshi Yamanaka; Kazuhiro Takuma; Yasuyuki Kita

Book ID
104225310
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
143 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

The Beckmann fragmentation is one of the long-known reacnons and used widely in organic syntbesis.l The reactive intermediates 2 in the Beckmann fragmentation of the corresponding a-alkoxycycloalkanone oxime denvatives are very active electrophdes.

Although they seem to react with many kinds of nucleophiles, only a limited land of nucleophiles such as H20, ROH, halide anion and carbon ones have been used so far.lz We wish to disclose here a novel hydride anion attack to 2. The overall transformation is shown in Scheme 1. This is, to our knowledge, the first example of reductive Beckmann fragmentation.

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