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Industrially, triethylborane is used as an initiator in radical reactions, where it is effective even at low temperatures. [1] As an initiator, it can replace some organotin compounds. It reacts with metal enolates , yielding enoxytriethylborates that can be alkylated at the α-carbon atom of the ketone more selectively than in its absence.
A borane is a compound with the formula BR x H y although examples include multi-boron derivatives. A large family of boron hydride clusters is also known. In addition to some applications in organic chemistry , the boranes have attracted much attention as they exhibit structures and bonding that differs strongly from the patterns seen in ...
These chemical compounds combine boron and carbon; typically, they are organic derivatives of borane (BH 3), as in the trialkyl boranes. [1] [2] Organoboranes and -borates enable many chemical transformations in organic chemistry — most importantly, hydroboration and carboboration.
Borane adducts are widely used in organic synthesis for hydroboration, where BH 3 adds across the C=C bond in alkenes to give trialkylboranes: [13] (THF)BH 3 + 3 CH 2 =CHR → B(CH 2 CH 2 R) 3 + THF. This reaction is regioselective. [14] Other borane derivatives can be used to give even higher regioselectivity. [15]
When only one functional group is present borylation occurs in the meta and para position in statistical ratios of 2:1 (meta:para). The ortho isomer is not detected due to the steric effects of the substituent. [16] Meta-para borylation. Addition of Bpin occurs in only one position for symmetrically substituted 1,2- and 1,4-substituted arenes.
The usual amount of the thickener is 6%. The amount of thickener can be decreased to 1% if other diluents are added. For example, n-hexane, can be used with increased safety by rendering the compound non-pyrophoric until the diluent evaporates, at which point a combined fireball results from both the triethylaluminium and the hexane vapors. [16]
Thexylborane is a borane with the formula [Me 2 CHCMe 2 BH 2] 2 (Me = methyl). The name derives from "t-hexylborane" (although the group is not the standard tert-hexyl group), and the formula is often abbreviated ThxBH 2. A colorless liquid, it is a monoalkylborane. It is produced by the hydroboration of tetramethylethylene: [1]
Tris(2,2,2-trifluoroethyl) borate can be prepared by reaction of trifluoroethanol with boron trichloride, borane dimethylsulfide, boron tribromide, or boric anhydride.The latter is more convenient for larger scale preparations due to its low cost and ease of handling.