REACTION OF SELENIUM MONOCHLORIDE WITH DIOLEFINS

The addition of selenium monochloride to olefins is known to lead to bis (β-chloroalkyl) selenides and free selenium. This reaction has now been studied on a variety of diolefins. Thus, cyclic selenides were obtained from linear diolefins, whereas bi- and tricyclic products were isolated from cyclic and bicyclic diolefins. Significant differences between the addition of selenium monochloride and sulfur dichloride were only apparent in reactions with conjugated olefins. The isolated products represent novel selenium-containing ring structures. The reaction provides a convenient synthesis of β,βȲ-substituted selenides for which, in most cases, no alternative synthesis is conceivable. © 1969, American Chemical Society. All rights reserved.