On August 20, 1999, Brown, Herbert C.; Kanth, Josyula V. B.; Dalvi, Pramod V.; Zaidlewicz, Marek published an article.Formula: C8H19NO2 The title of the article was Molecular Addition Compounds. 15. Synthesis, Hydroboration, and Reduction Studies of New, Highly Reactive tert-Butyldialkylamine-Borane Adducts. And the article contained the following:
Two series of tert-butyldialkylamines have been prepared and examined for borane complexation. The complexing ability of each amine in the two series examined decreases in the order shown. First series: t-BuN(CH2CH2)2O 1a > t-BuNEt2 1b > t-BuNPrn2 1c > t-BuN(CH2CH2OMe)2 1d ≫ t-BuNBui2 1e. Second series: t-BuNBuiMe 2a > t-BuNPriMe 2b > t-BuNBuiEt 2c > t-BuNBuiPrn 2d ≫ t-BuNPriEt 2e. The reactivity of the corresponding borane adducts toward 1-octene increases in the reverse order. The following amines form highly reactive liquid borane adducts hydroborating 1-octene in THF at room temperature in less than 1h: t-BuN(CH2CH2OMe)2, t-BuNBuiEt, and t-BuNPriMe. The limit of borane complexation among the amines examined is reached for t-BuNBui2 exchanging borane neither with BMS nor with BH3-THF. Among the various borane adducts prepared, the more promising borane adducts, t-Bu(CH3OCH2CH2)2N-BH3 (7), t-BuMePriN-BH3 (8), and t-BuEtBuiN-BH3 (9), were selected for complete hydroboration and reduction studies. Hydroboration studies with the new, highly reactive trialkylamine-borane adducts 7-9 and representative olefins, such as 1-hexene, styrene, β-pinene, cyclopentene, norbornene, cyclohexene, 2-methyl-2-butene, α-pinene, and 2,3-dimethyl-2-butene, in THF, dioxane, tert-Bu Me ether, n-pentane, and dichloromethane, at room temperature (22 ± 3°) were carried out. The reactions are faster in dioxane, requiring 1-2 h for the hydroboration of simple, unhindered olefins to the trialkylborane stage. Moderately hindered olefins, such as cyclohexene and 2-methyl-2-butene, give the corresponding dialkylboranes rapidly, with further slow hydroboration. However, the more hindered olefins, α-pinene and 2,3-dimethyl-2-butene, give stable monoalkylboranes very rapidly, with further hydroboration proceeding relatively slowly. The hydroborations can also be carried out conveniently in other solvents, such as THF, tert-Bu Me ether, and n-pentane. A significant rate retardation is observed in dichloromethane. Regioselectivity studies of 1-hexene and styrene using these amine-borane adducts show selectivities similar to that of BH3-THF. The rates and stoichiometry of the reaction of t-BuMePriN-BH3 in THF with selected organic compounds containing representative functional groups were also examined at room temperature The reductions of esters, amides, and nitriles, which exhibit a sluggish reaction at room temperature, proceed readily under reflux conditions in THF and dioxane and without solvent (at 85-90°). The carrier amines can be recovered by simple acid-base manipulations in good yield and readily recycled to make the borane adducts. The experimental process involved the reaction of 2,2′-(tert-Butylazanediyl)diethanol(cas: 2160-93-2).Formula: C8H19NO2
The Article related to butyldialkylamine borane adduct preparation hydroboration reduction reagent, Organometallic and Organometalloidal Compounds: Boron Compounds and other aspects.Formula: C8H19NO2
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