Kinetics and regioselectivity of ring opening of 1-bicyclo [3.1. 0] hexanylmethyl radical

…, CJ Hunt, KQ Barry-Holson, JP Lee…

Index: Kantorowski, Eric J.; Le, Daniel D.; Hunt, Caleb J.; Barry-Holson, Keegan Q.; Lee, Jessica P.; Ross, Lauren N. Journal of Organic Chemistry, 2008 , vol. 73, # 4 p. 1593 - 1596

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Citation Number: 3

Abstract

Rate constants for the rearrangement of 1-bicyclo [3.1. 0] hexanylmethyl radical (2) to 3- methylenecyclohexenyl radical (3) and 2-methylenecyclopentyl-1-methyl radical (1) were measured using the PTOC-thiol competition method. The ring-expansion pathway is described by the rate equation, log (k/s-1)=(12.5±0.1)-(4.9±0.1)/θ; the non-expansion pathway is described by log (k/s-1)=(11.9±0.6)-(6.9±0.8)/θ. Employing the slower trapping ...