Regio- and stereochemical regularities of electrophilic halogenation and chalcogenation of ethyl 2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate isomers
摘要
The electrophilic halogenation and chalcogenation (sulfenylation and selenenylation) of endo and exo isomers of ethyl 2-azabicyclo[2.2.1]hept-5-ene-3-carboxylates bearing electron-withdrawing substituents at the nitrogen atoms with different reagents were studied. Halogenation of both endo and exo isomers gave exclusively the rearranged products. Chalcogenation of endo isomer resulted in the rearranged products, while chalcogenation of exo isomer afforded the rearranged products and 1,2-trans and 1,2-cis addition products.