Allylic halides haloalkylation

Transformations cf sulfides and selenides to organic halides the haloalkylation and halopropenylation of alkyl and allyl halides... 

Allyl halides have been used to effect selective haloalkylations catalyzed by proton acids. For example, 3-chloropropylene reacts with benzene and toluene in the presence of H2SO4 to give haloalkyl-ated products almost exclusively (equation 87). The same result is obtained when ZnCh is used as Ae catalyst. ... 

Although some reactions, such as the transformation of -hydroxyalkyl selenides to -haloalkyl selenides (Scheme 161, b) or to vinyl selenides, enones (Scheme 161, 0. a,a-dihalocyclopropanes (Scheme 162, f) or p-hydroxyalkyl halides (Scheme 161, h Scheme 162, g), have bwn occasionally described or found only with specific types of -hydroxyalkyl selenides, especially those having a strained ring [e.g. their transformation to allyl selenides (Scheme 163, b), 1-selenocyclobutenes (Scheme 163, c) and cyclobutanones (Scheme 163, f),i2.i59,i60.i63] odiers are far more general. This is particularly the case of eir reductions to alcohols (Scheme 161, a Scheme 162, a Scheme 163, a Scheme 164, a Scheme 165, a) - or alkenes (Scheme 161, c Scheme 162, c Scheme 163, d Scheme 164, c Scheme 165, a Scheme 166, c), 89,i94,239 transformation to allyl alcohols (Scheme 161, e Scheme 162, b Scheme 164, b Scheme 166, b), - epoxides (Scheme 161, g Scheme 162, d Scheme 163, e Scheme 164, d Scheme 165, b Scheme 166, d) and rearranged carbonyl compounds (Scheme 162, e Scheme 164, e Scheme 165, a, c Scheme 166, e), - as well as oxidation to a-selenocarbonyl compounds (Scheme 161, d). 2 2.248-25i... 

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