Author/Authors :
Martيnez، نويسنده , , Antonio Garcيa and Vilar، نويسنده , , Enrique Teso and Fraile، نويسنده , , Amelia Garcيa and de la Moya Cerero، نويسنده , , Santiago and Ruiz، نويسنده , , Paloma Martيnez and Morillo، نويسنده , , Cristina Diaz and Maroto، نويسنده , , Beatriz Lora Maroto، نويسنده ,
Abstract :
Two different 1-amino-3,3-dimethyl-2-methylenenorbornane hydrochlorides, a primary ammonium chloride and a tertiary one, react unexpectedly with m-CPBA (meta-chloroperbenzoic acid) according to two different paths. The primary ammonium chloride gives place to a diastereomeric mixture of the corresponding spiranic 1-nitronorbornane-based epoxides, whereas the tertiary derivative undergoes a skeleton rearrangement giving 10-chlorocamphor. The results are interpreted in terms of competitive reaction pathways controlled by the nitrogenated group located at the C1 norbornane position.
