Y. Masuda, M. Hoshi, A. Arase
Dec 1, 1992
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
3-Chloro-1-iodo-1-propyne is smoothly hydroborated with dialkylboranes, giving (Z)-(3-chloro-1-iodo-1-propenyl)dialkylboranes exclusively. Subsequent treatment of the hydroboration mixture with sodium methoxide or aqueous sodium hydroxide results in migration of two alkyl groups from the boron atom to the α-alkenyl carbon atom to provide dialkylated allylboranes, which are protonolyzed with methanol or water to produce 1,1-dialkyl-1-propenes. Oxidation of the allylboranes with alkaline hydrogen peroxide prior to protonolysis gives 1,1-dialkyl-2-propen-1-ols. Treatment of (Z)-(3-chloro-1-iodo-1-propenyl)dicyclohexylborane with Grignard reagents, followed by protonolysis with acetic acid, provides 3-alkyl-3-cyclohexyl-1-propenes in which the alkyl group is derived from Grignard reagent.