Elucidation of the Vicarious Nucleophilic Substitution of Hydrogen Mechanism via Studies of Competition between Substitution of Hydrogen, Deuterium, and Fluorine

• Published in: Journal of organic chemistry Vol. 67; no. 2; pp. 394 - 400
• Main Authors: Ma̧kosza, Mieczysław, Lemek, Tadeusz, Kwast, Andrzej, Terrier, François
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 25.01.2002; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; NITROARENES; AMINATION; ALKYL HYDROPEROXIDE ANIONS; PHENYL SULFONES; HYDROXYLATION; SULFENAMIDES; ORGANIC-ANIONS; CARBANIONS; Deuterium; Sulfone; Fluorine; Hydrogen; E2 mechanism; Carbanion; Chlorides Organic compounds; Experimental study; Dehydrochlorination; Concentration effect; Reaction mechanism; Basic medium; Aromatic compound; Kinetics; Aromatic substitution; Nucleophilic substitution; SNAr mechanism

Relations of rates of the vicarious nucleophilic substitution of hydrogen (VNS) and SNAr substitution of fluorine in 2-fluoronitrobenzenes with chloroalkyl aryl sulfone carbanions were determined from competitive experiments carried out at various concentrations of base. The observed dependence of t...