[en] Although γ-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding γ-silyloxy-benzylselenides lead to a stereoisomeric mixture of γ-hydroxy-α-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration.
Disciplines :
Chemistry
Author, co-author :
Bousbaa, Jamal; Lab. de Chim. Organique de Synt., Department of Chemistry, Fac. Univ. Notre-Dame de la Paix, Namur, Belgium
Ooms, Frédéric ; Université de Liège - ULiège > HEC Liège Research > HEC Liège Research: Strategy & Performance for the Society ; Lab. de Chim. Organique de Synt., Department of Chemistry, Fac. Univ. Notre-Dame de la Paix, Namur, Belgium
Krief, Alain; Lab. de Chim. Organique de Synt., Department of Chemistry, Fac. Univ. Notre-Dame de la Paix, Namur, Belgium
Language :
English
Title :
γ-Siloxy-benzyllithiums: Stereochemistry of the retro-[1,4]-Brook rearrangement
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For some results involving the Brook and retro-Brook rearrangements : (a) Sammtleben, F.; Noltemeyer, M.; Brückner, R. Tetrahedron Lett. 1997, 32, 3893
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(d) Marumoto, S.; Kuwajima, I. J. Amer. Chem. Soc. 1993, 115, 9021
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(f) Marumoto, S.; Kuwajima, I. J. Amer. Chem. Soc. 1992, 114, 1421
