title: A facile route to diastereomeric phosphorus ylides. Chemoselective synthesis of dialkyl (E)-2-[1-(2-oxocyclopentylidene)ethyl]-2-butenedioates.
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.
authors.affiliation: Department of Chemistry, University of Mazandaran, P. O. Box 453, Babolsar, Iran. s.asghari@umz.ac.ir
authors.forename: Sakineh
authors.initials: S
authors.lastname: Asghari
authors.forename: Mohammad Bagher
authors.initials: MB
authors.lastname: Poushani
authors.forename: Samaneh
authors.initials: S
authors.lastname: Ramezani
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D006838:Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D006838:Hydrocarbons; D010758:Phosphorus