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

Sakineh Asghari* email, Mohammad Bagher Poushaniemail and Samaneh Ramezaniemail
Department of Chemistry, University of Mazandaran, P. O. Box 453, Babolsar, Iran
* Author to whom correspondence should be addressed.
Received: 24 December 2007; in revised form: 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.

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MDPI and ACS Style

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.

AMA Style

Asghari S, Poushani MB, Ramezani S. A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates. Molecules. 2008; 13(2):331-339.

Chicago/Turabian Style

Asghari, Sakineh; Poushani, Mohammad B.; Ramezani, Samaneh. 2008. "A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates." Molecules 13, no. 2: 331-339.

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