Radical-transfer catalysis versus Lewis acid catalysis by the copper(I) chloride/2,2′-bipyridine complex: an illustration of the synthetic significance of captodative radical stabilization
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 6,p. 857-858
- https://doi.org/10.1039/p29920000857
Abstract
The mechanism of the copper(I) chloride/2,2′-bipyridine catalysed π-cyclization of N-(chloromethyl)alk-3-enylcarbamates changes from a cationic process (leading to piperidines) into a radical-transfer process (leading to pyrrolidines) upon introduction of an ester substituent at the reactive carbon atom, owing to the captodative effect.Keywords
This publication has 16 references indexed in Scilit:
- N-Alkyl-5,5-dimethyl-2-oxomorpholin-3-yl radicals. Characterization and reaction with molecular oxygenJournal of the American Chemical Society, 1991
- Copper catalyzed chlorine transfer cyclizations of glycine and glycolic acid derivativesTetrahedron Letters, 1991
- Tin tetrachloride-induced π-cyclizations of glycine cation equivalents to substituted pipecolic acid derivativesTetrahedron, 1991
- Radical Addition ReactionsPublished by Elsevier ,1991
- Synthesis of cyclic α-amino acids through ring closure of glycine derived free radicalsTetrahedron Letters, 1990
- Radical stabilization energies and synergistic (captodative) effectsJournal of the American Chemical Society, 1989
- Highly stereoselective radical cyclization: copper or ruthenium-catalyzed preparation of cis- and trans-.beta.,.gamma.-dialkyl .gamma.-lactams from acyclic N-allyltrichloroacetamide derivativesThe Journal of Organic Chemistry, 1989
- Radical stabilization energies of disubstituted methyl radicals. A detailed theoretical analysis of the captodative effectJournal of the American Chemical Society, 1988
- The captodative effectAccounts of Chemical Research, 1985
- Copper-catalyzed additions of organic polyhalides to olefins: a versatile synthetic toolPublished by Walter de Gruyter GmbH ,1985