A stereoselective synthesis of conjugated dienes from alkynes via the hydroboration-iodination reaction

G Zweifel, NL Polston, CC Whitney

Index: Zweifel,G. et al. Journal of the American Chemical Society, 1968 , vol. 90, p. 6243 - 6245

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Citation Number: 68

Abstract

The hydroboration of 1-alkynes, such as 1-hexyne, with borane does not proceed to the trivinylborane stage, but results predominantly in the formation of 1, l-diboroalkanes. 3, 4 However, 1-hexyne reacts with thexylborane (2, 3-dimethyl-2-butylborane) to give the corresponding di~ inylthexylborane.~ Unfortunately, addition of iodine and sodium hydroxide to this divinylborane results in the migration of both the vinyl and the thexyl ...