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Synthesis 2001; 2001(3): 0437-0443
DOI: 10.1055/s-2001-11423
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Highly Efficient Conversion of Alcohols to Isocyanides

Yoshikazu Kitano* , Kazuhiro Chiba, Masahiro Tada
  • *Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan; Fax + 81(42)3 60 88 30; E-mail: kitayo@cc.tuat.ac.jp
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Publication Date:
31 December 2001 (online)

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Treatment of tertiary alcohols with silver salts (AgClO4, AgBF4, or AgOTf) and trimethylsilyl cyanide (TMSCN), followed by hydrolysis, directly affords excellent yields of corresponding isocyanides. This reaction proceeds selectively with tertiary alcohols in the presence of primary and secondary alcohols.

alcohols - isocyanides - silver salts - trimethylsilyl cyanide