Abstract
Borane adducts with selected N,N-dialkylanilines have been prepared and examined as hydroborating agents. The adduct H3B:NPhPri2 is a solid, considered less desirable than liquid adducts as hydroborating agents. Fortunately, the adducts H3B:NPhBuiMe, H3B:NPhPriMe, H3B:NPhPriEt, and H3B:NPhPriPrn are liquids above 0 °C, hydroborating 1-octene in tetrahydrofuran in less than 1 h at room temperature. Convenient procedures are described for generating gaseous diborane quantitatively, either by thermal dissociation of the borane−N,N-diisopropylaniline adduct or by the reaction of a 2.00 M solution of sodium borohydride in triglyme with a 5.40 M solution of boron trifluoride in triglyme.
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