Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Effect of the N-Substituent on the Course of the Reaction of α-Aminonitriles with Organometallic Reagents
Juji YoshimuraYoshiaki OhgoTetsuo Sato
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1965 Volume 38 Issue 11 Pages 1809-1813

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Abstract

The reactions between various N-substituted-α-aminonitriles and organometallic reagents have been investigated in order to clarify the effect of the N-substituent on the reaction course.
The results indicate that:
(1) Both Grignard reagent and lithium alkyl attack not nitrile carbon but α-carbon to give substituted product when the α-aminonitrile has an active hydrogen on its aminonitrogen.
(2) In the case of α-dialkylaminonitriles, Grignard reagents attack the α-carbon to give substituted products, but lithium alkyls attack the nitrile carbon.
(3) The aminonitriles bearing acetyl group on its aminonitrogen are not attacked at α-carbon but at nitrile carbon by both the reagents, thus giving addition products.

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