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Methyllithium-Promoted Wittig Rearrangements of α-Alkoxysilanes

Robert E. Maleczka, Jr.* and Feng Geng

*Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, Email: maleczkacem.msu.edu

R. E. Maleczka, Jr., F. Geng, Org. Lett., 1999, 1, 1115-1118.

DOI: 10.1021/ol990912+ (free Supporting Information)


Abstract

Depending on both the substrate and reaction conditions employed, α-alkoxysilanes underwent [2,3]-, [1,2]-, or [1,4]-Wittig rearrangements promoted by the action of methyllithium. These rearrangements were shown to be initiated by either Si/Li exchange or deprotonation to the silane.

see article for more reactions

proposed mechanism



Synthesis and Fluoride-Promoted Wittig Rearrangements of α-Alkoxysilanes

R. E. Maleczka, Jr., F. Geng, Org. Lett., 1999, 1, 1111-1113.


Key Words

[1,2]-Wittig Rearrangement, [2,3]-Wittig Rearrangement


ID: J54-Y1999-500