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Synlett 1991; 1991(4): 238-240
DOI: 10.1055/s-1991-20691
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New Synthetic Method for Allylic Isocyanates Through [3,3] Sigmatropic Rearrangement of Allylic Cyanates

Yoshiyasu Ichikawa*
  • *Faculty of Education, Mie University, Tsu, Mie 514, Japan
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Publication Date:
07 March 2002 (online)

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Dehydration of allylic carbamates has been proved to be an effective method for the synthesis of allylic cyanates, which immediately rearrange to allylic isocyanates at or below ambient temperature. The allylic isocyanates (6 examples) were characterized by further reaction with pyrrolidine to provide stable and easily isolable ureas. This process offers a useful synthetic tool for the construction of the allylic amine moiety from allylic alcohols. The efficiency, scope and limitations of this new method were examined.