Synthesis of Functionalized Diorganyl Selenides from Selenium Dihalides and Allylic Aromatic Compounds

Abstract

Hitherto unknown addition and methoxyselenation reactions of selenium dihalides with methyl eugenol and allyl naphth-1-yl ether were studied. The addition and methoxyselenation reactions of selenium dihalides with methyl eugenol led mainly to Markovnikov products, while the formation of anti-Markovnikov products prevailed in the reactions with allyl naphth-1-yl ether. Families of novel functionalized selenides, including bis[3-(3,4-dimethoxyphenyl)-2-methoxy- and -2-haloprop-1-yl] selenides, bis[3-(3,4-dimethoxyphenyl)-1-methoxy- and -1-haloprop-2-yl] selenides, bis[3-(naphth-1-yl)-1-methoxy- and -1-haloprop-1-yl] selenides, bis[3-(naphth-1-yl)-2-methoxy- and -2-haloprop-1-yl] selenides, were synthesized.