Isobutyl alcohol halides

Isobutyl halides and other isobutyl compounds rearrange readily to tert-butyl compounds for the older literature see Whitmore and Lux.869 However, PBr3 (see page 223) converts isobutyl alcohol into isobutyl bromide in good yield with less than 1% of tert-butyl bromide.869... 

The following qualitative observations on the action of liquid ammonia on organic compounds are mainly by E. C. Franklin and C. A. Kraus, those in brackets are by G. Gore. Aliphatic compounds.—Halides methyl iodide, m. chloroform, reacts, and m. bromoform, m. iodoform, v.s., ethyl bromide and iodide, s. ethylene bromide, s. ethylidene chloride, m. isobutyl bromide, s. amyl bromide, s.s. tribromomethane, v.s. nitrotriohloromethane, m. perehloroethane (n.s.) perchloroethylene (m.) dichloroacetylene (s.). Alcohols methyl, m. ethyl, m. propyl, m. normal butyl,... 

Only with reagents that attack all available carbon-aluminum bonds (H2O, D2O, O2, X2, SO2, etc.) will the hydroalumination of alkenic substrates and the derivatization of such adducts prove useful. That two of three C—Al bonds of adduct (23) are expended in the formation of side products, which have to be separated, may be an acceptable price to pay for the convenient, high-yielding generation of a desired specifically deuteriated reduction product, (24) or (25), ° primary alcohol (26), primary halide (27) or sulfinic acid. Of course the isobutylated side products should, in each case, be easily separable (Scheme 6). 

---