Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and Water

Abstract

Environmentally friendly synthetic methods were developed for the selective preparation of new 2,3-dihydro-1,4-thiaselenine derivatives in high yields based on the reactions of 2-bromomethyl-1,3-thiaselenole with alcohols and water at room temperature. The reaction of 2-bromomethyl-1,3-thiaselenole with alcohols was accompanied by a rearrangement with ring extension, leading to six-membered heterocyclic compounds, a new family of 2-organyloxy-2,3-dihydro-1,4-thiaselenines, in 80–96% yields. The remarkable cascade reactions of 2-bromomethyl-1,3-thiaselenole with water afforded 2,3-dihydro-1,4-thiaselenines functionalized with the (Z)-S-CH=CH-Se fragment and one or two highly reactive aldehyde groups. The latter aldehydes were functionalized by the reactions with alcohols and glycols to give new polyfunctionalized compounds, containing two double bonds, two sulfur atoms, two selenium atoms, and two or four oxygen atoms, in high yields.

Keywords

• alcohols
• 2-bromomethyl-1,3-thiaselenole
• dihydro-1,4-thiaselenine derivatives
• heterocyclic compounds
• nucleophilic reactions
• water