Electrochemical preparation of tris(tert-butyldimethylsilyl)cyclopropene and its hydride abstraction to tris(tert-butyldimethylsilyl)cyclopropenium tetrafluoroborate

H A Buchholz; G K Prakash; D Deffieux; G A Olah

doi:10.1073/pnas.96.18.10003

Electrochemical preparation of tris(tert-butyldimethylsilyl)cyclopropene and its hydride abstraction to tris(tert-butyldimethylsilyl)cyclopropenium tetrafluoroborate

Proc Natl Acad Sci U S A. 1999 Aug 31;96(18):10003-5. doi: 10.1073/pnas.96.18.10003.

Authors

H A Buchholz¹, G K Prakash, D Deffieux, G A Olah

Affiliation

¹ Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA.

Abstract

Electrochemical reductive tert-butyldimethylsilylation of tetrachlorocyclopropene to 1,2,3-tris(tert-butyldimethylsilyl)cyclopropene, a potential strained precursor for Diels-Alder and related cycloaddition reactions, is described. By hydride abstraction with nitrosonium tetrafluoroborate, 1,2,3-tris(tert-butyldimethylsilyl)cyclopropene is ionized quantitatively to Hückeloid 2pi aromatic tris(tert-butyldimethylsilyl)cyclopropenium tetrafluoroborate.