Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Reaction of N-Substituted Carbonimidic Dihalides with Grignard Reagents. The Generation of Alkyl or Aryl Halides from Grignard Reagents
Sakuya TanakaMasaya OkanoShigeo Tanimoto
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1975 Volume 48 Issue 6 Pages 1862-1864

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Abstract

The reaction of N-alkyl- or N-aryl-carbonimidic dihalides with Grignard reagents afforded α-elimination products, isocyanides, rather than substitution ones. Two kinds of alkyl or aryl halides were produced concomitantly in this reaction: one kind consisted of halides generated from the Grignard reagents used, and the other, of halides the halogens of which had been derived from the dihalides. The ease of formation of these halides was found to decrease in the order: iodide>bromide>chloride, regardless of which substrate served as the source of a halogen atom. A probable reaction mechanism is proposed.

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