NEW ROUTE TO SELENOACETALS - EXCHANGE-REACTION BETWEEN ACETALS AND TRIS-(PHENYLSELENO)BORANE

We report a new method for preparing selenoacetals (1, Rʺ = Ph), a class of compounds that promises to be very useful in organic synthesis.1 These substances are reduced smoothly by triphenyltin hydride (1→2), and this process, taken together with the conversion of a carbonyl compound into a selenoacetal, constitutes an alternative to the classical Wolf-Kishner reduction.2 Selenoacetals are converted by the action of butyllithium into selenium-stabilized carbanions (1→3) which can be used, inter alia, for making carboncarbon bonds1-3 and for preparing sulfur-stabilized carbanions that are not available by deprotonation. © 1979, American Chemical Society. All rights reserved.