Aldol-type condensation vs. vinyl selenide formation from selenoacetals

KM Nsunda, L Hevesi

Index: Nsunda, K. M.; Hevesi, L. Journal of the Chemical Society, Chemical Communications, 1987 , # 20 p. 1518 - 1520

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Abstract

Rapid addition of a tertiary amine to tin(iv) chloride-selenoacetal mixtures leads to the corresponding vinyl selenides in good yield, whereas slow addition of the amine base gives aldol condensation products. ... Selenium-stabilised carbocationic species have proved valu- able electrophiles in carbon-carbon bond-forming reactions. 1 However, carbenium ions bearing heteroatomic substituents on the positively charged carbon may follow other reaction paths, depending ...