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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

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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. 2-Acetylcyclopentanone; phosphorus ylides; spirocompounds; intramolecular Wittig reaction.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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