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Molecules 2008, 13(2), 331-339; doi:10.3390/molecules13020331
Article

A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates

* ,
 and
Department of Chemistry, University of Mazandaran, P. O. Box 453, Babolsar, Iran
* Author to whom correspondence should be addressed.
Received: 24 December 2007 / Revised: 21 January 2008 / Accepted: 21 January 2008 / Published: 7 February 2008
(This article belongs to the Special Issue Spiro Compounds)
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Abstract

2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphineand dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinates. These compounds undergo intramolecularWittig reactions in boiling benzene to produce highly strained spirocyclobutenederivatives, which spontaneously undergo ring-opening reactions to produce dialkyl (E)-2-[1-(2-oxocyclopentyliden)ethyl]-2-butenedioates.
Keywords: 2-Acetylcyclopentanone; phosphorus ylides; spirocompounds; intramolecular Wittig reaction. 2-Acetylcyclopentanone; phosphorus ylides; spirocompounds; intramolecular Wittig reaction.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Asghari, S.; Poushani, M.B.; Ramezani, S. A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates. Molecules 2008, 13, 331-339.

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