title: Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine.
abstract: To explore the ambident electrophilic reactivity of dimethyl carbonate (DMC), reactions with the ambident nucleophile phenylhydrazine were investigated. When a Brönsted base was used, selective carboxymethylation occurred at N-1, after that several other compounds were produced selectively utilizing various conditions. Formation of these compounds was explained by using the Hard-Soft Acid-Base (HSAB) theory. Catalysis by some metal salts altered the reactivity of phenylhydrazine, which effected selective carboxymethylation at N-2 of phenylhydrazine instead.
authors.affiliation: Consorzio Interuniversitario Nazionale La Chimica per l'Ambiente, 21/8 Via delle Industrie, Marghera VE, 30175, Italy.
authors.forename: Anthony E
authors.initials: AE
authors.lastname: Rosamilia
authors.forename: Fabio
authors.initials: F
authors.lastname: Arico
authors.forename: Pietro
authors.initials: P
authors.lastname: Tundo