usually produced in less than 10%. A notable case with lower regioselectivity is styrene, and the selectivity is strongly influenced by the substituent on the para position. Hydroboration of 1,2-disubstituted alkenes, such as a cis or trans olefin, produces generally a mixture of the two organoboranes of comparable amounts, even if the substituents are very different in terms of steric bulk. For such 1,2-disubstituted olefins, regioselectivity can be observed only when one of the two substituents is a phenyl ring. In such cases, such as trans-1-phenylpropene, the boron atom is placed on the carbon adjacent to the phenyl ring. The observations above indicate that the addition of H-B bond to olefins is under electronic control rather than steric control. Reactions of organoboranes The C-B bonds generated by hydroboration are reactive with various reagents, the most common one being hydrogen peroxide. Because the addition of H-B to olefins is stereospecific, this oxidation reaction will be diastereoselective when the alkene is trisubstituted. Hydroboration-oxidation is thus an excellent way of producing alcohols in a stereospecific and anti-Markovnikov fashion. Hydroboration can also lead to amines by treating the intermediate organoboranes with monochloramine or O-hydroxylaminesulfonic acid (HSA). Terminal olefins are converted to the corresponding alkyl bromides and alkyl iodides by treating the organoborane intermediates with bromine or iodine. Such reactions have not however proven very popular, because succinimide based reagents such as NIS and NBS are more versatile and do not require rigorous conditions as do organoboranes. etc. Borane adducts Diborane can be produced in situ by reduction BF3 with NaBH4 (see for Flavopiridol). Usually however, borane dimethylsulfide complex BH3S(CH3)2 (BMS) is used as a source of BH3. It can be obtained in highly concentrated forms. The adduct BH3(THF) is also commercially available as THF solutions wherein it exists as the 1:1 adduct. It degrades with time. Borane adducts with phosphines and amines are also available, but are not widely used. Borane makes a strong adduct with triethylamine; using this adduct requires harsher conditions in hydroboration. This can be advantageous for cases such as hydroborating trienes to avoid polymerization. More sterically hindered tertiary and silyl amines can deliver borane to alkenes at room temperature. Monosubstituted boranes Monoalkyl boranes are relatively rare. When the alkyl group is small, such as methyl, the monoalkylboranes tend to redistribute to give mixtures of diborane and di- and trialkylboranes. Monoalkylboranes typically exist as dimers of the form [RBH2]2. One example