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Vol. 33, No. 13, pp. 2187–2196, 2003
Solvent Effect in the Wittig Reaction
Under Boden’s Conditions
Enrique M. Pandolfi,
*
Gloria V. Lo´pez,
Eduardo Dı´as, and Gustavo A. Seoane
Departamento de Quı´mica Orga´nica, Facultad de
Quı´mica, Universidad de la Repu´blica, Montevideo,
Uruguay
ABSTRACT
An interesting change in the stereochemical outcome of the Wittig
olefination reaction under Boden’s conditions (potassium bases and
18-crown-6 as the ylide forming reagent) is reported. This effect
depends significantly on the polarity of the solvents and the nature
of the ylide.
Key Words: Stereochemical control; Wittig olefination.
*Correspondence: Enrique M. Pandolfi, Departamento de Quı´mica Orga´nica,
Facultad de Quı´mica, Av. Gral. Flores 2124, 11800, Universidad de la
Repu´blica, Montevideo, Uruguay; E-mail: epandolf@fq.edu.uy.
2187
DOI: 10.1081/SCC-120021496 0039-7911 (Print); 1532-2432 (Online)
Copyright & 2003 by Marcel Dekker, Inc. www.dekker.com