The stereochemistry of an allyl cyanate-to-isocyanate rearrangement has been investigated by employing a chiral allyl carbamate. The rearrangement has been found to be stereospecific and the chirality of an allyl cyanate is transformed into that of an allyl isocyanate. This result shows that an allyl cyanate-to-isocyanate rearrangement is a concerted reaction involving a cyclic transition state.
Y. Ichikawa, K. Tsuboi and M. Isobe, J. Chem. Soc., Perkin Trans. 1, 1994, 2791 DOI: 10.1039/P19940002791
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