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Paper | Regular issue | Vol 31, No. 8, 1990, pp.1445-1450
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5321
The [3+2] Intramolecular Cycloaddition Reaction of Azomethine Ylides Generated from Benzylic N-Oxides

Georges Roussi

*Institut des Chimie des Substances Naturelles, C.N.R.S., 1 avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France


Benzylic azomethine ylides (Y) generated by deprotonation of the corresponding tertiary amine N-oxides (1a, 1b, 4) react intramolecularly with the suitably positioned unactivated double bond to yield the corresponding fused membered pyrrolidines (2a, 2b, 5). A competitive evolution of the ylide is observed at low temperature leading to the corresponding head to head piperazines (3, 6, 8).