Free-Radical Carbon-Carbon Bond Formation in Organic Synthesis
Author:
- 2 March 1984
- journal article
- research article
- Published by American Association for the Advancement of Science (AAAS) in Science
- Vol. 223 (4639) , 883-887
Abstract
Organic chemists have begun to use intra- and intermolecular free-radical addition reactions to develop useful synthetic transformations. Carboncentered radicals can form bonds with electron-rich or electron-deficient alkenes, allenes, and acetylenes. Radical addition reactions can also be used to construct hindered carbon-carbon bonds. These characteristics, as well as the large number of functional groups that tolerate free-radical conditions contribute to the importance of such reactions in organic synthesis.Keywords
This publication has 64 references indexed in Scilit:
- Vinyl radical cyclization. 2. Dicyclization via selective formation of unsaturated vinyl radicals by intramolecular addition to triple bonds. Applications to the synthesis of butenolides and furansJournal of the American Chemical Society, 1983
- Hydroxymercuration-reductive coupling route to .delta.-lactones. Synthesis of malyngolide, an antibiotic from a marine blue-green algaOrganometallics, 1982
- Reductive cyclizations involving attack of radical anions derived from ketones, aldehydes and enones on isolated carbon-carbon triple and double bonds. Application of frontier molecular orbitalsThe Journal of Organic Chemistry, 1981
- Methods of Reactivity UmpolungAngewandte Chemie International Edition, 1979
- Cyclization of 5-hexenyl radicalsJournal of the American Chemical Society, 1972
- Facile reaction of organoboranes with acrolein. Convenient new aldehyde synthesis via hydroborationJournal of the American Chemical Society, 1967
- Radical Cyclizations in the Reaction of Trialkyltin Hydrides with Alkenyl Halides1Journal of the American Chemical Society, 1966
- A New Cyclization. 2-Methylenecyclopentanols by the Chemical Reduction of γ-Ethinyl KetonesJournal of the American Chemical Society, 1965
- Some Radical Reactions of Trivalent Phosphorus Derivatives with Mercaptans, Peroxides, and Olefins. A New Radical CyclizationJournal of the American Chemical Society, 1964
- Free-Radical Cycloadditions to cis,cis-1,5-CyclooctadieneJournal of the American Chemical Society, 1964