1998 organo-selenium compounds, acyclic C derivatives

organo-selenium compounds, acyclic C derivativesS 0132

32 - 231Protecting Groups for Organoselenium Compounds. — It is shownthat -CONEt2, -COOEt2, and COMe are efficient protecting groups for organo-selenium compounds. Alkyl and aryl selenocarbamates, selenocarbonatesand selenoacetates can easily be prepared by either reductive cleavage of thecorresponding diselenides or lithium-halogen exchange from aryl halides andselenium insertion, followed by capping with the appropriate protecting group.Selenocarbamates are stable to a variety of reducing agents and nucleophilesbut are efficiently deprotected by NaOH. Selenocarbonates and -acetates aresmoothly deprotected by aq. NH4OH. Unfortunately, Pd-catalyzed couplingreactions employing these protected compounds are unsuccessful. — (REIN-ERTH, W. A.; TOUR, J. M.; J. Org. Chem. 63 (1998) 7, 2397-2400; Dep.Chem. Biochem., Univ. S. C., Columbia, SC 29208, USA; EN)

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