Regioselective One-Pot Synthesis of Novel Functionalized Organoselenium Compound by Bis-Alkoxyselenenylation of Alkenes with Selenium Dibromide and Alcohols

Abstract

The one-pot efficient synthesis of novel functionalized organoselenium compound by bis-alkoxyselenenylation of alkenes with selenium dibromide and alcohols was developed. The reaction of the selenium dibromide with cyclopentene or cyclohexene in the system alcohol/sodium bicarbonate/methylene chloride at room temperature afforded bis(2-alkoxycycloalkyl) selenides in 90–99% yields. The regioselective and efficient method for bis-alkoxylation of terminal alkenes was developed based on the addition of selenium dibromide with 1-alkenes in acetonitrile followed by refluxing of addition products in alcohols in the presence of traces of sulfuric acid. This method made it possible to selectively obtain bis(2-alkoxyalkyl) selenides in 94–98% yields.

Keywords

• alcohols
• alkenes
• selenium dibromide
• alkoxyselenenylation
• selenium dihalides
• cycloalkenes