ABSTRACT The addition of halogen hybrids, HX [H = 1H, 2H; X = F, Cl, Br, I], to alkenes and alkynes has long been accepted as a paradigm for electrophilic addition to unsaturated systems (de la Mare, 1966, 1982). This review, which concentrates on recent experimental and theoretical work reported on such additions, avoids repeating the broader efforts of Sergeev, et al. (Sergeev, 1983), Schmid (Schmid, 1978, 1989), Khirstove, et al. (Khristove, 1991), and Larock and Leong (Larock, 1991), except as required for perspective. Further, although weakly bound HX complexes with unsaturated systems have long been known (Cook, 1956; Novick, 1990), the recent isolation and x-ray crystal structure determination of just such molecular complexes [i.e., between hydrogen chloride and 2-butyne by Mootz and Deeg (Mootz, 1992)] has lent new impetus to detailed investigation of the paths by which such addition may occur.
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