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

2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphine and dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-λ(5)-phosphanylidene)succinates. These compounds undergo intra-molecular Wittig reactions in boiling benzene to produce h...

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Detalles Bibliográficos
Autores principales: Asghari, Sakineh, Poushani, Mohammad Bagher, Ramezani, Samaneh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2008
Materias:
Full Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245385/
https://www.ncbi.nlm.nih.gov/pubmed/18305421
http://dx.doi.org/10.3390/molecules13020331
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author Asghari, Sakineh
Poushani, Mohammad Bagher
Ramezani, Samaneh
author_facet Asghari, Sakineh
Poushani, Mohammad Bagher
Ramezani, Samaneh
author_sort Asghari, Sakineh
collection PubMed
description 2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphine and dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-λ(5)-phosphanylidene)succinates. These compounds undergo intra-molecular Wittig reactions in boiling benzene to produce highly strained spirocyclobutene derivatives, which spontaneously undergo ring-opening reactions to produce dialkyl (E)-2-[1-(2-oxocyclopentyliden)ethyl]-2-butenedioates.
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spelling pubmed-62453852018-11-26 A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates Asghari, Sakineh Poushani, Mohammad Bagher Ramezani, Samaneh Molecules Full Paper 2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphine and dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-λ(5)-phosphanylidene)succinates. These compounds undergo intra-molecular Wittig reactions in boiling benzene to produce highly strained spirocyclobutene derivatives, which spontaneously undergo ring-opening reactions to produce dialkyl (E)-2-[1-(2-oxocyclopentyliden)ethyl]-2-butenedioates. MDPI 2008-02-07 /pmc/articles/PMC6245385/ /pubmed/18305421 http://dx.doi.org/10.3390/molecules13020331 Text en © 2008 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Full Paper
Asghari, Sakineh
Poushani, Mohammad Bagher
Ramezani, Samaneh
A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates
title A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates
title_full A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates
title_fullStr A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates
title_full_unstemmed A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates
title_short A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates
title_sort facile route to diastereomeric phosphorus ylides. chemoselective synthesis of dialkyl (e)-2-[1-(2-oxocyclopentylidene)ethyl]-2-butenedioates
topic Full Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245385/
https://www.ncbi.nlm.nih.gov/pubmed/18305421
http://dx.doi.org/10.3390/molecules13020331
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