Determining the σ-donor ability of the cyclopropane C–C bond

Organic & Biomolecular Chemistry Pub Date: 2005-04-11 DOI: 10.1039/B503124A

Abstract

The low temperature crystal structures of ester and ether derivatives of varying electron demand, derived from cyclopropylmethanol 8 and dicyclopropylmethanol 9, have been determined. These structures show a very strong response of the C–OR bond distance to the electron demand of the OR substituent, demonstrating the strong σ-donor ability of the strained C–C bonds in the cyclopropane ring.

Graphical abstract: Determining the σ-donor ability of the cyclopropane C–C bond
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