MOLECULAR ADDITION-COMPOUNDS - 10 - BORANE ADDUCTS WITH N,N-DIALKYLANILINES FOR HYDROBORATION

Borane adducts with selected N,N-dialkylanilines have been prepared an d examined as hydroborating agents. The adduct H3B:NPhPr2i is a solid, considered less desirable than liquid adducts as hydraborating agents , Fortunately, the adducts H3B:(NPhBuMe)-Me-i, H3B: (NPhPrMe)-Me-i, H3 B:(NPhPrEt)-Et-i, and H3B:(NPhPrPrn)-Pr-i are liquids above 0 degrees C, hydroborating 1-octene in tetrahydrofuran in less than 1 h at room temperature. Convenient procedures are described for generating gaseou s diborane quantitatively, either by thermal dissociation of the boran e-N,N-diisopropylaniline adduct or by the reaction of a 2.00 M solutio n of sodium borohydride in triglyme with a 5.40 M solution of boron tr ifluoride in triglyme.