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Small Ring Compounds in Organic Synthesis II pp 1–75Cite as

Synthesis and synthetic applications of 1-metallo-1-selenocyclopropanes and -cyclobutanes and related 1-metallo-1-silylcyclopropanes

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 135))

Abstract

Among the α-heterosubstituted cyclopropylmetals α-selenocyclopropyllithiums represent some of the most valuable synthetic intermediates. They are quantitatively prepared from selenoacetals of cyclopropanones and butyllithiums, are thermally stable at ∼−78° for several hours and are particularly nucleophilic especially towards carbonyl compounds. The cyclopropyl derivatives containing a selenenyl moiety have been transformed to selenium free derivatives such as alkylidene cyclopropanes, vinyl cyclopropanes, allylidene cyclopropanes, cyclobutanones and α-silyl cyclopropyllithiums. The latter compounds have been used as starting material for the synthesis of alkylidene cyclopropanes and cyclopentenyl derivatives. α-Seleno cyclobutyllithiums, which are available in two steps from cyclobutanones, also permit the synthesis of various selenium free homologues such as alkylidene cyclobutanes, vinyl cyclobutanes, oxaspirohexanes and cyclopentanones.

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  1. Départment de Chimie, Facultés Universitaires de Namur, Rue de Bruxelles 61, 5000, Namur, Belgium

    Alain Krief

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Krief, A. (1987). Synthesis and synthetic applications of 1-metallo-1-selenocyclopropanes and -cyclobutanes and related 1-metallo-1-silylcyclopropanes. In: de Meijere, A. (eds) Small Ring Compounds in Organic Synthesis II. Topics in Current Chemistry, vol 135. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-16662-9_3

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