title: Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A Convenient Synthon for the Preparation of Substituted 1,4-Thiazepin-5-ones and Piperidinones via the Intermediacy of Thioacids.
abstract: Reaction of thiomaleic anhydride with triphenylphosphine gives the title compound which undergoes reaction with a variety of aldehydes to give a range of alkylidene thiomaleic anhydrides (substituted monothio itaconic anhydrides). Subsequent treatment with tert-butoxycarbonylamino-substituted thiols, or under radical conditions with tert-butoxycarbonylamino-substituted alkyl halides results in a series of substituted monothiomaleic anhydrides, that on exposure to trifluoroacetic acid and then base lead to thiocarboxyl substituted 1,4-thiazepin-5-ones and piperidinones, respectively, that are ultimately trapped by reaction with 2,4-dinitrobenzenesulfonamides to give the corresponding amides.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: David
authors.initials: D
authors.lastname: Crich
authors.forename: Md Yeajur
authors.initials: MY
authors.lastname: Rahaman