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Regioselective syntheses of bis-(2-haloalkyl) selenides in excellent yields were developed based on selenium dihalides and terminal alkenes (1-hexene, 1-heptene and 1-octene). The addition of selenium dichloride and dibromide to the alkenes occurred via the intermediate formation of kinetic products, anti-Markovnikov bis-(1haloalk-2-yl) selenides, which were further transformed into thermodynamically stable Markovnikov products presumably via seleniranium intermediates. Preparations of dihalo[bis-(2-haloalkyl)]-λ-selanes in 95-99% yields were accomplished by halogenation of bis-(2-haloalkyl) selenides. The system MeOH / NaHCO3 / CH2Cl2 was developed for methoxyselenenylation of the alkenes using selenium dibromide leading to bis-(2-methoxyalkyl) and bis-(1-methoxyalk-2-yl) selenides in 68-80% total yields.

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Regio-selective syntheses of bis(2-haloalkyl) selenides and dihalo[bis(2-haloalkyl)]-λ4-selanes from selenium dihalides and 1-alkenes and the methoxyselenenylation reaction