Journal of the American Chemical Society

Cyclopentane construction by dirhodium tetraacetate-mediated intramolecular CH insertion: steric and electronic effects

DF Taber, RE Ruckle

Index: Taber,D.F.; Ruckle,R.E. Journal of the American Chemical Society, 1986 , vol. 108, p. 7686

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Citation Number: 244

Abstract

Abstract: Factors which govern the regiospecificity of cyclopentane formation by rhodium (I1) acetate mediated intramolecular CH insertion (1-2) have been studied. The order of reactivity of the target CH site is found to be methine> methylene> methyl. Allylic and benzylic CH are found to be less reactive than aliphatic CH. These results are interpreted as being due to the availability of the electron density in the CH bond. Steric influences on ...