is thexylborane (ThxBH2), produced by the hydroboration of tetramethylethylene: B2H6 + 2 Me2C=CMe2 → [Me2CHCMe2BH2]2 A chiral example is monoisopinocampheylborane. Although often written as IpcBH2, it is a dimer [IpcBH2]2. It is obtained by hydroboration of (−)‐α‐pinene with borane dimethyl sulfide. Species of the form RBH2 are available for R = alkyl and halide. Monobromo- and monochloro-borane can be prepared from BMS and the corresponding boron trihalides. The stable complex of monochloroborane and 1,4-dioxane effects hydroboration of terminal alkenes. Disubstituted boranes Dimesitylborane dimesitylborane is a dimer (C6H2Me3)2B2H2). It reacts only slowly with simple terminal alkenes. On the other hand, alkynes undergo monohydroboration with Mes2BH easily to produce alkenylboranes. Disiamylborane Among hindered dialkylboranes is disiamylborane, abbreviated Sia2BH. It also is a dimer. Owing to its steric bulk, it selectively hydroborates less hindered, usually terminal alkenes in the presence of more substituted alkenes. Disiamylborane must be freshly prepared as its solutions can only be stored at 0 °C for a few hours. Dicyclohexylborane Chx2BH exhibits improved thermal stability than Sia2BH. 9-BBN A versatile dialkylborane is 9-BBN. Also called "banana borane", it exists as a dimer. It can be distilled without decomposition at 195 °C (12mm Hg). Reactions with 9-BBN typically occur at 60–80 °C, with most alkenes reacting within one hour. Tetrasubstituted alkenes add 9-BBN at elevated temperature. Hydroboration of alkenes with 9-BBN proceeds with excellent regioselectivity. It is more sensitive to steric differences than Sia2BH, perhaps because of it rigid C8 backbone. 9-BBN is more reactive towards alkenes than alkynes. Other secondary boranes Simple, unhindered dialkylboranes are reactive at room temperature towards most alkenes and terminal alkynes but are difficult to prepare in high purity, since they exist in equilibrium with mono- and trialkylboranes. One common way of preparing them is the reduction of dialkylhalogenoboranes with metal hydrides. An important synthetic application using such dialkylboranes, such as diethylborane, is the transmetallation of the organoboron compounds to form organozinc compounds. Pinacolborane and catecholborane For catalytic hydroboration, pinacolborane and catecholborane are widely used. They also exhibit higher reactivity toward alkynes. Pinacolborane is also widely used in a catalyst-free hydroborations. See also Hydroboration–oxidation reaction References Organic reactions