Preparative Organic Chemistry
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ChemInform Abstract: Through-Bond Transmission of Substituent Effects in the Bicyclo(2.2.2)octane Ring System: Solvolysis of 4-Deuterio- and 4-Metalloidal (M(CH3)3, M: Si, Ge, and Sn)-Substituted Bicyclo(2.2.2)oct-1-yl p-Nitrobenzenesulfonates and Methanesulfonates
First published: August 7, 1990
ChemInform Abstract
(kinetics of the solvolysis of (I) and (II) in aqueous EtOH and trifluoroethanol; extraordinarily large H/D isotope effect (1.048-1.050) over five single bonds; stabilization of the intermediate cation derived from (II) by through-bond coupling (or double hyperconjugation)).
