Journal of the American Chemical Society

Selenium stabilized anions. Synthetic transformations based on propargyl selenoxides

HJ Reich, SK Shah

Index: Reich,H.J.; Shah,S.K. Journal of the American Chemical Society, 1977 , vol. 99, # 1 p. 263 - 265

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Citation Number: 42

Abstract

Heterosubstituted propargyl and allenyl organolithium reagents have potential as synthetic precursors to highly functionalized 3-carbon fragments.'We report here the preparation of the dianion 1, 2 and reactions of the propargyl selenides derived from it (Scheme I). Phenyl propargyl selenide is rapidly deprotonated by 2 equiv of lithium diisopropylamide in tetrahydrofuran or glyme at-78" C to give a pale yellow solution of the dilithium reagent l. 3 ...

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