Masahiro Kato, I. Kuwajima
Mar 1, 1984
Citations
0
Influential Citations
20
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
1-(Trimethylsilyl)propargyl alcohols have been prepared by treating acyltrimethylsilanes with magnesium acetylides, and their base-induced reactions involving rearrangement of silyl group have been examined. Treatment of the alcohol with an equimolar amount of butyllithium in hexane followed by addition of tetrahydrofuran has allowed to generate the lithiated 3-trimethylsiloxy-1,2-propadiene, which reacts with an alkyl iodide to afford the alkylated 1-trimethylsiloxy-1,2-propadiene in high yield. Further, a catalytic amount of butyllithium also effects an efficient conversion of the alcohol to the corresponding 1-siloxy-1,2-propadiene through a similar rearrangement process.