Journal of Organic Chemistry p. 7320 - 7322 (1991)
Update date:2022-08-02
Topics: Rearrangement Kinetic Study Chemical Reaction Experimental procedure Rate of reaction
Gibbs, Leslie W.
Wedegaertner, Donald K.
The thermal rearrangement of triphenylacetonitrile oxide (1a) to triphenylmethyl isocyanate (2) is a first-order process.Rate constants at five temperatures between 116 and 190 deg C were determined giving ΔH(excit.) = 9.3 +/- 1.1 kcal/mol and ΔS(excit.) = -58.2 +/- 2.4 cal/mol*K.The rearrangement of substituted triarylacetonitrile oxides (1b-d) occur only slightly faster than that of 1a.These results are interpreted in terms of a concerted single-step rearrangement in which the highly ordered transition state (6c) has a degree of radical character.
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