25125-85-3Relevant articles and documents
Eliminative ring opening of oxiranium ions in the gas phase
Renzi, Gabriele,Roselli, Graziella,Grandinetti, Felice,Filippi, Antonello,Speranza, Maurizio
, p. 1673 - 1676 (2007/10/03)
An unprecedented reaction governed by stereoelectronic factors: Eliminative ring opening of epoxides, unknown in acidic Solution owing to the predominance of the competing nucleophilic displacement, can be made accessible in the gas phase. The kinetic evidence, supported by a comprehensive theoretical study on a model system, points to a concerted elimination mechanism in which stereochemistry is controlled by stereoelectronic and conformational factors (in the scheme, the E isomer is formed more readily than the Z isomer; k(E) > k(Z)).