1,1‐Disilyl Alcohols as d¹ Synthons: Harnessing the 1,2‐Brook Rearrangement.

Abstract

Organo-silicon compoundsOrgano-silicon compounds S 0060 1,1-Disilyl Alcohols as d 1 Synthons: Harnessing the 1,2-Brook Rearrangement.-In the presence of base, 1,1-disilyl alcohols such as (III) undergo 1,2-Brook rearrangement. Carbanions are formed which can be trapped with alkyl halides to afford silyl ethers of type (V) and (IX). The latter smoothly undergo oxidation to ketones revealing the full capacity of the rearrangement system as an acyl anion equivalent. Double 1,2-Brook rearrangement-alkylation is also possible as is shown by formation of the silyl ether (XII). -(FLEMING*, I.; LAWRENCE, A. J.; RICHARDSON, R. D.; SURRY, D. S.; WEST, M. C.; Helv. Chim. Acta 85 (2002) 10, 3349-3365; Dep. Chem., Univ. Cambridge, Cambridge CB2 1EW, UK; Eng.) -Jannicke 11-173 2003 Organo-silicon compounds