PMID: 11312979Apr 21, 2001Paper

Comparison between electron transfer and nucleophilic reactivities of ketene silyl acetals with cationic electrophiles

The Journal of Organic Chemistry
Shunichi FukuzumiJunzo Otera

Abstract

The products and kinetics for the reactions of ketone silyl acetals with a series of p-methoxy-substituted trityl cations have been examined, and they are compared with those of outer-sphere electron transfer reactions from 10,10'-dimethyl-9,9', 10, 10'- tetrahydro-9,9'-biacridine [(AcrH)2] to the same series of trityl cations as well as other electron acceptors. The C-C bond formation in the reaction of beta,beta-dimethyl-substituted ketene silyl acetal (1: (Me2C=C(OMe)OSiMe3) with trityl cation salt (Ph3C+ClO4-) takes place between 1 and the carbon of para-positon of phenyl group of Ph3C+, whereas a much less sterically hindered ketene silyl acetal (3: H2C=C(OEt)OSiEt3) reacts with Ph3C+ at the central carbon of Ph3C+. The kinetic comparison indicates that the nucleophilic reactivities of ketene silyl acetals are well correlated with the electron transfer reactivities provided that the steric demand at the reaction center for the C-C bond formation remains constant.

Citations

Oct 17, 2008·Chemistry : a European Journal·Günther Knör
Mar 16, 2013·Chemistry : a European Journal·Jerome R RobinsonEric J Schelter
Apr 3, 2016·Chembiochem : a European Journal of Chemical Biology·Aoi TakedaYasuteru Urano
Nov 28, 2013·Journal of the American Chemical Society·Jerome R RobinsonEric J Schelter
Mar 13, 2003·Chemical Reviews·Alexander D Dilman, Sema L Ioffe
Apr 14, 2018·Organic Letters·Kazuki UrakawaHayato Ishikawa
Jan 8, 2003·Journal of the American Chemical Society·Shinya Minegishi, Herbert Mayr
Feb 28, 2004·The Journal of Organic Chemistry·Rajendra RathoreIlia A Guzei

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