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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.
The reaction is much slower with ketones than aldehydes. [40] For example, in Nicolaou's epothilones synthesis, asymmetric allylboration (with an allylborane derived from chiral alpha-pinene) is the first step in a two-carbon homologation to acetogenin: [41] Trifluoroborate salts are stabler than boronic acids and selectively alkylate aldehydes ...
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 ...
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]
Triethyl borate is a colorless liquid with the formula B(OCH 2 CH 3) 3.It is an ester of boric acid and ethanol.It has few applications. [1]It is a weak Lewis acid (AN = 17 as measured by the Gutmann–Beckett method). [2]
Regiospecific hydroboration with borane Hydroboration-oxidation of (E)-prop-1-en-1-ylbenzene Hydroboration-oxidation of 1-methyl-cyclohex-1-ene. The net reaction is hydration. Because the addition of H-B to olefins is stereospecific, this oxidation reaction will be diastereoselective when the alkene is trisubstituted. [10]
This reaction is known as Goldberg modified Ullmann condensation. [44] In 2003, R. A. Batey and T. D. Quach have modified this kind of reactions by using potassium organotrifluoroborates salts to react with aliphatic alcohols, aliphatic amines or anilines to synthesize aryl ethers or aryl amines. [45] [46]
Triethyloxonium tetrafluoroborate is prepared from boron trifluoride, diethyl ether, and epichlorohydrin: [5] 4 Et 2 O·BF 3 + 2 Et 2 O + 3 C 2 H 3 OCH 2 Cl → 3 [Et 3 O] + [BF 4] − + B(OCH(CH 2 Cl)CH 2 OEt) 3. where the Et stands for ethyl. The trimethyloxonium salt is available from dimethyl ether via an analogous route. [6]