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Quantitating the Effect of an Ortho Substituent on Cyclization and Intramolecular Hydrogen-Transfer Reactions of Aryl Radicals

Quantitating the Effect of an Ortho Substituent on Cyclization and Intramolecular Hydrogen-Transfer Reactions of Aryl Radicals

Dennis P Curran, Neil Fairweather

J Org Chem. 2003 Apr 4;68(7):2972-4.

PMID: 12662080

Abstract:

Reduction of allyl 2-iodobenzyl malonates with triphenyltin hydrides generates aryl radicals that partition between 6-exo cyclization, 7-endo cyclization, and 1,5-hydrogen atom transfer. Rate constants for all of these processes are high (>10(8) M(-)(1) s(-)(1)), and the rates are only marginally reduced (<33%) by the introduction of methyl group ortho to the reacting radical.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP76631	Allyltriphenylstannane		76-63-1	Price

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