
%0 Journal Article
%A Raner, KD 
%A Skelton, BW 
%A Ward, AD 
%A White, AH 
%T Reactions of Epoxides Derived From 2&#8242;-(3&#8243;-Methylbut-2&#8243;-enyl)trifluoroacetanilides
%J Australian Journal of Chemistry
%D 1990/03/01
%V 43
%N 3
%P 609-616
%K 
%R https://doi.org/10.1071/CH9900609
%U https://www.publish.csiro.au/paper/CH9900609 
%X The intramolecular nucleophilic ring opening of the epoxides derived from 2&#8242;-(3&#8243;-methylbut-2&#8243;-enyl) trifluoroacetanilides has been investigated under both acidic and basic conditions. Boron trifluoride caused rearrangement of the epoxides to a ketone but no cyclization. Potassium carbonate in methanol caused regiospecific opening of the epoxides and generated dihydroindole products. The formation of a five-membered ring was confirmed by a single-crystal X-ray study of one of the products. The epoxides  hydrolysed very readily in acidic conditions; the structure of one of the diol products was confirmed by a single-crystal X-ray study. 
