Chemoselective Reduction of Organoselenocyanates to Diselenides

✍ Scribed by Alain Krief*; Cathy Delmotte; Willy Dumont

• Book ID: 104256913
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 293 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00549-2

✦ Synopsis

Selenocyanatespossessan extremely high propensityto produce diselenides on reaction with selenols or selenolates.This is effectivelyobservedwhen one molar equivalent of metal hydride or lithium triethyl borohydride or one fourth molar equivalent of metal borohydridesare reactedwith organic selenocyanates.01997 publishedby ElsevierScienceLtd.

Organoselenocyanates play an important role in organoselenium chemistry. They are readily available and stable compounds which are easily transformed to valuable basic organoselenium reagents or compoundsl especially to selenols and selenolates. The first transformation has been for long carried out with hypophosphorousacid2a-c and the second one with sodium borohydride2d-e (Scheme 1, left). More recently Salama described3 that lithium triethyl borohydride and diisobutyl aluminum hydride produce either selenols or selenolates depending upon the amount (1 or 2 equivalents) of reducing agent used (Scheme 1, right).