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Synlett 1999; 1999(3): 288-290
DOI: 10.1055/s-1999-2615
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A Direct Conversion of Alkenes 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 1999 (online)

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Treatment of alkenes with silver salts (AgClO4, AgBF4, or AgOTf) and trimethylsilyl cyanide (TMSCN) in dichloromethane followed by hydrolysis affords the corresponding isocyanides directly in high yields. The addition of the isocyano function is carried out in accordance with Markovnikov's rule.

addition reactions - alkenes - isocyanides