A facile route to diastereomeric phosphorus ylides. Chemoselective synthesis of dialkyl (E)-2-[1-(2-oxocyclopentylidene)ethyl]-2-butenedioates

Sakineh Asghari; Mohammad Bagher Poushani; Samaneh Ramezani

doi:10.3390/molecules13020331

A facile route to diastereomeric phosphorus ylides. Chemoselective synthesis of dialkyl (E)-2-[1-(2-oxocyclopentylidene)ethyl]-2-butenedioates

Molecules. 2008 Feb 7;13(2):331-9. doi: 10.3390/molecules13020331.

Authors

Sakineh Asghari¹, Mohammad Bagher Poushani, Samaneh Ramezani

Affiliation

¹ Department of Chemistry, University of Mazandaran, P. O. Box 453, Babolsar, Iran. s.asghari@umz.ac.ir

Abstract

2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphine and dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-lambda(5)-phosphanylidene)succinates. These compounds undergo intramolecular 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.

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry
Hydrocarbons / chemical synthesis*
Hydrocarbons / chemistry
Phosphorus / chemistry*
Stereoisomerism

Substances

Alkenes
Hydrocarbons
Phosphorus