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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 2
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Original Articles

PHOSPHONIUM YLIDE-CATALYZED CYCLOTRIMERIZATION OF ETHYL PROPYNOATE

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Pages 297-304 | Received 04 Dec 2000, Published online: 16 Aug 2006
 

ABSTRACT

The cyclotrimerization of ethyl propynoate (2) to yield aromatic triesters is shown to proceed via consecutive [2 + 2] cycloadditions of ethoxycarbonylmethylenetriphenylphosphonium ylide (1) to three moles of (2), followed by cyclization and elimination of (1).

ACKNOWLEDGMENTS

We thank Mr HSC Spies for the NMR spectra and many helpful discussions and Ms V Truter for the mass spectra. Technical assistance by Mr MC de Jongh and his staff is gratefully acknowledged.

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