Halogen nucleophilic

Reaction with Halogen Nucleophiles. Hydrochloric acid [7647-01-0] hydrobromic acid [10035-10-6] and hydroiodic acid [10034-85-2] react readily with ethyleneimine (3) to give the corresponding P-halogenoethylamines (20,21). 

Scheme 2.39 Ring-opening reactions with halogen nucleophiles.

The application of the amidrazone method is limited. Most of the other published preparations are equally divided between electrophilic halogenation, nucleophilic displacement of halogen or nitro groups, and displacement of diazo or nitrosamino groups. The conversion of triazolinones into chlorotriazoles with phosphorus chlorides may be regarded as a nucleophilic displacement reaction of the hydroxytriazole tautomer, while the preparation of chlorotriazoles by the action of chlorine on thiones is regarded as oxidative chlorination. 

Tin-carbon bonds can be broken by reaction with electrophiles (e.g. protic acids, Lewis acids, halogens), nucleophiles (e.g. RLi), or free radicals (e.g. succimidyl, t-butoxyl), or with certain transition metal (particularly palladium) compounds. Fragmentation can also be induced through the radical cations which are formed by electron transfer. 

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