Six-vs Seven-Membered Ring Formation from the 1-Bicyclo [4.1. 0] heptanylmethyl Radical: Synthetic and ab Initio Studies

EJ Kantorowski, SWE Eisenberg…

Index: Kantorowski, Eric J.; Eisenberg, Shawn W. E.; Fink, William H.; Kurth, Mark J. Journal of Organic Chemistry, 1999 , vol. 64, # 2 p. 570 - 580

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Citation Number: 11

Abstract

The viability of utilizing 1-bicyclo [4.1. 0] heptanylmethyl radical (3) to serve as a progenitor of seven-membered carbocycles was examined. Rate constants for the rearrangement of this radical to 3-methylenecycloheptyl radical (4) and 2-methylenecyclohexyl-1-methyl radical (6) were measured using the competition method of 3 with thiophenol over the temperature range of-75 to 59° C. Arrhenius functions were calculated for the conversions ...

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