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

Buchholz, H A; Prakash, G K; Deffieux, D; Olah, G A · Proc Natl Acad Sci U S A · 1999

basic_science · Level V

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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.