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Synthesis 2011(24): 3997-4002  
DOI: 10.1055/s-0031-1289592
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Isocyanides from Alcohols

Iku Okada, Yoshikazu Kitano*
Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo 183-8509, Japan
Fax: +81(42)3675700; e-Mail: kitayo@cc.tuat.ac.jp;
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Publication History

Received 30 August 2011
Publication Date:
04 November 2011 (online)

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Abstract

A one-pot reaction of alcohols with trimethylsilyl cyanide and methanesulfonic acid with subsequent neutralization by triethylamine and dehydration by tosyl chloride and pyridine gave the corresponding isocyanides in moderate-to-high yields. This method was used to synthesize tertiary and benzylic isocyanides from the corresponding alcohols.

Key words

isocyanides - alcohols - Ritter reactions

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