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-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.
Asghari
Sakineh
S
Department of Chemistry, University of Mazandaran, P. O. Box 453, Babolsar, Iran. s.asghari@umz.ac.ir
Poushani
Mohammad Bagher
MB
Ramezani
Samaneh
S
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D006838:Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D006838:Hydrocarbons; D010758:Phosphorus