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Pinacolborane is the borane with the formula (CH 3) 4 C 2 O 2 BH. Often pinacolborane is abbreviated HBpin. [1] It features a boron hydride functional group incorporated in a five-membered C 2 O 2 B ring. Like related boron alkoxides, pinacolborane is monomeric. It is a colorless liquid. [2] It features a reactive B-H functional group. [3]
Pinacolborane is a closely related reagent. The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkanes and alkenes. Using various organorhodium or organoiridium catalysts, it can also be installed onto saturated hydrocarbons: [3] CH 3 (CH 2) 6 CH 3 + [pinB] 2 → pinBH + CH 3 (CH 2) 7 Bpin. These reactions proceed via ...
They have the formula L n M-BR 2 or L n M-(BR 2 LB) (L = ligand, R = H, organic substituent, LB = Lewis base). One example is (C 5 Me 5)Mn(CO) 2 (BH 2 PMe 3) (Me = methyl). [2] Such compounds, especially those derived from catecholborane and the related pinacolborane, are intermediates in transition metal-catalyzed borylation reactions.
This colourless liquid is a derivative of catechol and a borane, having the formula C 6 H 4 O 2 BH. Synthesis and structure ... Pinacolborane adopts a similar structure.
The stoichiometry and idealized regiochemistry of hydroboration of terminal alkenes follows: BH 3 + 3 RCH=CH 2 → B(CH 2 −CH 2 R) 3. In reality, each hydroboration step follows 1,2-addition but ca. 4% gives the 2,1 addition (affording the B(CH(CH3)R isomer). [1]
Pinacol is a branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction.
A boronic acid is an organic compound related to boric acid (B(OH) 3) in which one of the three hydroxyl groups (−OH) is replaced by an alkyl or aryl group (represented by R in the general formula R−B(OH) 2). [1] As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes.
9-Borabicyclo[3.3.1]nonane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroboration reagent.The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates.