Selenium-stabilized anions. Preparation of. alpha.,. beta.-unsaturated carbonyl compounds using propargyl selenides. Synthesis of (.+-.)-7-hydroxymyoporone

HJ Reich, SK Shah, PM Gold…

Index: Reich, Hans J.; Shah, Shrenik K.; Gold Paul M.; Olson Richard E. Journal of the American Chemical Society, 1981 , vol. 103, # 11 p. 3112 - 3120

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Citation Number: 63

Abstract

Abstract: The reaction of alkyl halides, carbonyl compounds, and trimethylsilyl chloride with the mono-and dianion (1) prepared by deprotonation of phenyl propargyl selenide with lithium diisopropylamide gives 1-or 3-monosubstituted or 1, 3-disubstituted propargyl selenides (a). Oxidation to selenoxides (3b) results in rearrangement to 2-(phenylseleno)-l, 3-disubstituted propenones. The rate of rearrangement of propargyl selenoxides ...

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