Borane adducts of selected trialkylamines with isopropyl and isobutyl groups of intermediate steric requirements have been prepared and examined as hydroborating agents. Their
reactivity toward 1-octene follows the order i-Pr2NEt·BH3 < i-Bu3N·BH3 < i-PrNBu
i
2·BH3
< i-Pr2NCH2CH2OMe·BH3 < i-Pr2NBu
i
·BH3 < i-Pr3N·BH3 < i-Pr2NBu
s
·BH3. Borane adducts
with i-Pr2NBu
i
, i-Pr3N, and i-Pr2NBu
s
are highly reactive, hydroborating 1-octene in THF
at room temperature in less than 1 h. The adduct i-Pr2NBu
i
·BH3 is a liquid above 0 °C, 4.6
M in BH3, stable over long periods, and soluble in diethyl ether, tert-butyl methyl ether,
tetrahydrofuran, dioxane, dichloromethane, and n-pentane. The adduct i-Pr3N·BH3 is a solid,
while i-Pr2NBu
s
·BH3 is a liquid, unstable, slowly evolving diborane at room temperature.
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