Organoboranes. I. Isomerization and displacement reactions of organoboranes. A convenient procedure for the conversion of internal olefins into primary alcohols
HC Brown, BCS Rao
Index: Brown; Subba Rao Journal of the American Chemical Society, 1959 , vol. 81, p. 6434,6437
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Citation Number: 28
Abstract
The hydroboration of 2-hexene yields an orgdnoborane which, oxidized directly without prior isolation, yields 2-and 3-hexanol in equimolar amounts. However, if the organoborane is heated in refluxing diglyme (160") for four hours prior to oxidation, the product obtained is essentially pure 1-hexanol. In the same manner 2-octene, mixed 2-, 3-, 4-and 5-decenes, and a similar mixture of tetradecenes have been converted into 1-octanol, 1-decanol and ...
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