Reaction of Organic Selenocyanates with Hydroxides: The One-Pot Synthesis of Dialkyl Diselenides from Alkyl Bromides

The amount of hydroxide used in the reaction with organic selenocyanate determines the identity of the product (see scheme). Dialkyl and diaryl diselenides are efficiently prepared with 0.5 equivalents of hydroxide, whereas the reaction of aryl selenocyanates with at least one molar equivalent of hydroxide leads to the formation of aryl selenolates. R = Ph, Bu, iPr, PhCH2; M = Li, Na, K.