Fade substitution reactions at the tertiary carbon of p-nitrocumyl chloride and a,p-dinitrocumene are described. These reactions occur with a wide range of organic and inorganic nucleophiles and are noteworthy for providing novel and powerful means of synthesis; they occur readily under mild conditions, give excellent yields of pure products, and, in contrast to SN2 displacements, are rather insensitive to steric hindrance. They are, therefore, especially valuable for the preparation of highly branched compounds. The view that these are electron-transfer chain processes derives from inhibition studies and, also, from the fact that these reactions are induced by one-electron-transfer agents. (1) Substitution Reactions Which Proceed via Radical Anion Intermediates. 29. Part 2 8 Kornblum, N.; Kelly, W. J.; Kestner, M. M. J. Org. Chem. 1985,50, 4720. This paper is based on the doctoral dissertations of the 12 junior authors. Reference to these theses is made by employing the initials of the author and the date of the thesis. Preliminary communications have appeared in:
7) Presumably, the alcohol derives from the oxygen alkylate, but (8) In addition, m-nitro-cu-methylstyrene is isolated in 12 Z yield.(9) These and other differences are discussed briefly in the accompanying communication:
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