Tetrahedron

Photolysis of olefinic N-chloropyrrolidinones, N-chlorosuccinimides and N-chloro-oxazolidinones: Reactivity of cyclic carboxamidyl, imidyl and carbamyl radicals in …

B Daoust, J Lessard

Index: Daoust, Benoit; Lessard, Jean Tetrahedron, 1999 , vol. 55, # 12 p. 3495 - 3514

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Citation Number: 27

Abstract

N-Chloro-alkenylpyrrolidinones, an N-chloro-alkenylsuccinimide and N-chloro- alkenyloxazolidinones were prepared as precursors of olefinic cyclic carboxamidyl, imidyl and carbamyl radicals constrained to undergo intramolecular reactions uniquely via their planar or slightly twisted (30–35°) ΠN state (1, 5-transfer of an allylic hydrogen, 5-exo or 6- exo cyclization to give bicyclo [2.2. 1] azaheptane and bicyclo [3.2. 1] azaoctane skeletons ...