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

• Published in: Russian journal of organic chemistry Vol. 55; no. 8; pp. 1153 - 1159
• Main Authors: Musalov, M. V., Yakimov, V. A., Potapov, V. A., Amosova, S. V., Zinchenko, S. V.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.08.2019; Springer Nature; Springer Nature B.V
• Subjects: Aromatic compounds; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Organic Chemistry; Physical Sciences; Science & Technology; Selenides; Selenium; allyl naphth-1-yl ether; selenium dihalides; methyl eugenol; diorganyl selenides; methoxyselenation
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428019080141

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.