Cyclopropylcarbinyl cation chemistry and antihomoaromaticity in the cycloprop [2, 3] inden-1-yl cation system

EC Friedrich, DB Taggart, MA Saleh

Index: Friedrich,E.C. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 8 p. 1437 - 1443

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Citation Number: 23

Abstract

A detailed investigation of the solvolytic behaviors of the endo-and ero-cycloprop [2, 3] inden- l-yl3, 5-dinitroben-zoates in 80% aqueous acetone has been carried out. Both esters exhibited closely similar rates of hydrolysis and gave identical mixtures of endo-and ero- cycloprop [2, 3] inden-l-ol products. From kinetic comparisons with model systems, it could be concluded that antihomoaromatic effects cause a rate retardation at 80" C of ...