
TY  - JOUR
A1  - Raner, KD 
A1  - Skelton, BW 
A1  - Ward, AD 
A1  - White, AH 
T1  - Reactions of Epoxides Derived From 2&#8242;-(3&#8243;-Methylbut-2&#8243;-enyl)trifluoroacetanilides
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1990
VL  - 43
IS  - 3
SP  - 609
EP  - 616
KW  - 
UR  - https://doi.org/10.1071/CH9900609 
N2  - 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. 
ER  -

