Interconversion of 1-methylene-3-vinylcyclopentane and 5-methylenecycloheptene. A Cope rearrangement

SJ Rhoads, JM Watson…

Index: Rhoads,S.J. et al. Journal of the American Chemical Society, 1978 , vol. 100, # 16 p. 5151 - 5155

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Citation Number: 9

Abstract

Abstract: 1-Methylene-3-vinylcyclopentane (3) and 5-methylenecycloheptene (4) undergo first-order interconversion in the temperature range 260-300 OC with AH&7= 35.5 & 1.0 kcal/mol for the reactions 3-+ 4 and 4-3 and=-16.6 f 3.0 eu for the reaction 3-4 and-12.7 f 3.0 eu for the reaction 4-3. A study of the conversion of 4, labeled with deuterium at the exo- methylene group, to 3, labeled exclusively in the five-membered ring, establishes the ...