Volume 31, Issue 12
Isocyclic Compounds
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ChemInform Abstract: Coupling Reactions. Part 21. Synthesis of Functionalized Bi(cyclopropylidenes).

Rolf Huwyler

Rolf Huwyler

Inst. Chem. Biochem., Univ. Bern, CH-3012 Bern, Switz.

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Ahmad Al-Dulayymi

Ahmad Al-Dulayymi

Inst. Chem. Biochem., Univ. Bern, CH-3012 Bern, Switz.

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Markus Neuenschwander

Markus Neuenschwander

Inst. Chem. Biochem., Univ. Bern, CH-3012 Bern, Switz.

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First published: 09 June 2010

Abstract

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ChemInform Abstract

In the search for novel triafulvalene precursors, a series of bi(cyclopropylidenes) (II) is prepared by copper-catalyzed dimerization of the corresponding dibromocyclopropane derivatives (I). However, the synthesis of carboxy-substituted bi(cyclopropylidene), a suitable precursor for dibromo-bi(cyclopropylidene), is not achieved, neither by direct dimerization reaction nor by hydrolysis of alkoxycarbonyl analogues (IIb)—(IId) nor by oxidation of hydroxymethyl analogue (III). Finally, direct synthesis of acetoxy-substituted bi(cyclopropylidene) (VI), bearing suitable leaving groups for triafulvalene formation, is achieved, although in low yield.

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