Halides, alkyl, reaction with succinimide

Simple alkyl halides can be prepared by radical halogenation of alkanes, but mixtures of products usually result. The reactivity order of alkanes toward halogenation is identical to the stability order of radicals R3C- > R2CH- > RCH2-. Alkyl halides can also be prepared from alkenes by reaction with /V-bromo-succinimide (NBS) to give the product of allylic bromination. The NBS bromi-nation of alkenes takes place through an intermediate allylic radical, which is stabilized by resonance. 

This reaction is analogous to 10-16. Primary and secondary alcohols can be converted to alkyl aryl sulfides (ROH RSAr) in high yields by treatment with BU3P and an V-(arylthio)succinimide in benzene. Thioethers RSR can be prepared from an alcohol ROH and a halide R Cl by treatment with tetra-methylthiourea Me2NC(=S)NMe2 followed by NaH. ... 

Numerous derivatives of imidazoline nitroxides with various functional groups have been obtained in the investigations of reactions of 4-alkyl-halide- and 4-alkyl-dihalide-3-imidazoline-3-oxides. The interaction of compounds 7a,b with an equimolar quantity of iV-bromo- and N-chloro-succinimide leads to 4-bromomethyl-, 4-a-bromoethyl-, and 4-a-chloro-ethyl-3-imidazoline-3 oxides (64a,b) (Kutikova and Volodarsky, 1973 Grigor ev and Volodarsky, 1975). With the addition of excess iV-succinimide halide 4-dibromomethyl-, 4-dichloromethyl-, and 4-a,a-dichloroethyl-3-imidazoline-3-oxides (65a,b) are formed (Grigor ev and Volodarsky, 1974 Grigor ev et a/., 1975 Mitasov et ai, 1978). Nitroxides 64 and 65 are reduced by zinc to diamagnetic 1-hydroxy-derivatives 66 and 67. 

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