title: One-pot regioselective synthesis of nitrophenyloxazolinyl styrene oxides by the Darzens reaction of vicarious nucleophilic substitution-formed carbanions of 2-dichloromethyl-4,4-dimethyloxazoline.
abstract: The vicarious nucleophilic substitution reaction of dichloromethyloxazoline 2 with nitrobenzene has been investigated. Treatment of 2 with t-BuOK followed by the addition of nitrobenzene leads to benzylic carbanions 4 or 9 depending upon the solvent used (DMSO, DMF, or THF). Subsequent treatment of 4 or 9 with aldehydes, in a Darzens-like reaction, furnishes very good yields of nitrophenyl oxazolinyloxiranes 8 and 11. 1,2-Dioxazolinyl-1,2-dinitrophenylethene 7 forms quantitatively when carbanion 4 is allowed to warm to room temperature in the absence of external electrophiles.
authors.affiliation: Dipartimento Farmaco-Chimico, University of Bari, Via E. Orabona 4, I-70126 Bari, Italy. florio@farmchim.uniba.it
authors.forename: Saverio
authors.initials: S
authors.lastname: Florio
authors.forename: Patrizia
authors.initials: P
authors.lastname: Lorusso
authors.forename: Catia
authors.initials: C
authors.lastname: Granito
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
authors.forename: Luigino
authors.initials: L
authors.lastname: Troisi