Aliphatic Bis(acyl) Selenides — Synthesis and Characterization

Abstract

Bis(acyl) Selenide, Carboxylic Acid Selenoanhydride A series of aliphatic bis(acyl) selenides 1 were isolated from the reaction of acyl chlorides with sodium selenide and characterized.In gen eral, the chalcogeno isologues of aliphatic carboxylic acid derivatives are less stable than the arom atic ones therm ally and tow ards oxygen. In fact, though several arom atic bis(acyl) selenides have b een isolated as crystals [1]. O nly one aliphatic d e rivative has been described by Jensen and H endriksen w ho isolated bis(ethanecarbonyl) selenide in low yield from the reaction of propanoyl chloride with hydrogen selenide [2], In the course of our studies concerning selenocarboxylic acid derivatives, a series of aliphatic bis(acyl) selenides w ere required. H erein we wish to re p o rt the isolation and characterization of sim ple aliphatic bis(acyl) selenides 1 .A series of aliphatic bis(acyl) selenides 1 were iso lated in good yields from the reaction of sodium selenide w ith tw o equivalents of acyl chloride in e th e r (eq. (1)). F or exam ple, a solution of propanoyl chloride (22 m m ol) in e th e r (10 ml) was added to sodium selenide (11 m m ol) and the m ixture was stir red at 15 °C for 10 h. T he precipitates was rem oved by filtration and the solvent was evap o rated under reduced p ressure. D istillation of the residue in vacuo afforded 84% of bis(ethanecarbonyl) selenide l b . Sim ilarly, the reaction w ith o th e r acyl chlorides af

Reactions of acyl chlorides with LiAlHSeH. Preparation of diacyl selenides, diacyl diselenides, selenocarboxylates and cyclic selenoanhydrides

“…So far it has been relatively difficult to obtain aliphatic diacyl selenides 3 because of their instability. 3c, 4 The present reaction gave even lower aliphatic diacyl selenides, i.e. diacyl selenides bearing methyl, ethyl and propyl groups, in moderate to good yields.…”