Novel features of the 1,3 rearrangement of S-(–)-N-(1-phenylethyl)diphenylvinylideneamine to S-(–)-2,2,3-triphenylbutyronitrile

Abstract

S-(–)-N-(1-phenylethyl)diphenylvinylideneamine (1) rearranges, apparently quantitatively, to S-(–)-2,2,3-triphenylbutyronitrile (2) in CCl₄, k(2·9 ± 0·3)× 10^–4 s^–1, and CD₃CN, k(3·9 ± 0·4)× 10^–4 s^–1, at 60 °C with partial retention of configuration at the migrating centre; N-(benzyl)diphenylvinylideneamine (8) undergoes a similar rearrangement, but N-(t-butyl)diphenylvinylidene amine (9) yields only disproportionation type products, at a higher temperature (125 °C).