723254-62-4Relevant academic research and scientific papers
Ambident reactivity of the cyanate anion
Schaller, Heike F.,Schmidhammer, Uli,Riedle, Eberhard,Mayr, Herbert
, p. 3866 - 3868 (2008)
A study was conducted to investigate ambident reactivity of the cyanate anion. The study showed that the cyanate anion is an ambident nucleophile, which may react with electrophiles either at the oxygen terminus, to yield alkyl cyanates, or at the nitrogen terminus, to yield isocyanates. Equal amounts of alkyl cyanates and isocyanates were obtained, when secondary iodoalkynes were treated with silver cyanate and the formation of tert-butyl isocyanate, along with 2-methylpropene and cyanic acid. The study also investigated the possibility of SN1 reactions of cyanates proceeding with charge control to give cyanates.
