Journal of Organic Chemistry p. 754 - 756 (1982)
Update date:2022-08-11
Topics:
Brown, Herbert C.
Basavaiah, D.
Dialkylboranes, generated in situ via hydridation of dialkylhaloboranes, hydroborate 1-bromo-1-alkynes to provide cleanly B-(cis-1-bromo-1-alkenyl)dialkylboranes.Treatment of these intermediates with sodium methoxide results in the migration of one of the alkyl groups on boron to the adjacent carbon, displacing the bromine, providing B-(trans-1-alkyl-alkenyl)alkylborinate esters.These intermediates provide ketones on oxidation, stereospecific trans alkenes on protonolysis, and trisubstituted alkenes on iodination, all in high yields.
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