Thallium in organic synthesis. XXXVIII. Oxidation of chalcones, deoxybenzoins, and benzoins with thallium(III) nitrate (TTN)

Abstract

Treatment of chalcones with 3 equiv of thallium(III) nitrate (TTN) in aqueous acidic glyme results in formation of benzils by means of a discrete series of three independent oxidations involving the intermediacy of deoxybenzoins and then benzoins. This reaction constitutes a simple and convenient method for the synthesis

Síntese da fenitoína assistida por micro-ondas: proposta de aula prática para alunos de graduação

“…A oxidação da benzoína à sua respectiva alfa-dicetona, a benzila, é um método relativamente simples e amplamente descrito na literatura com o uso de diversos agentes oxidantes, como ácido nítrico, 24 solução de Fehling, 25 nitrato de tálio (III), 26 acetato de nitrato-cobre (II) e bismuto (III), 27 sais de cromo com alumina ácida, 28 dentre outros. Mais recentemente, foi relatada uma reação de oxidação para a benzoína empregando-se hidreto de sódio, 29 resultando em um rendimento elevado e sem o emprego de reagentes tóxicos, numa busca por um processo sintético mais limpo e seguro do ponto de vista ambiental.…”

Metal-ion oxidations in solution. Part XX. The mechanism of the reaction of thallium (III) with 2-mercaptosuccinic acid in perchlorate media

“…The stoichiometry of the reaction was determined by spectrophotometric titration of the unreacted thiomalic acid present in the mixture (14 [2] and [4], and [3] and [5] as to the route for formation of [T1SRHI2+. An equilibrium similar to [5] has been favoured, however, in the oxidation of H 2 0 2 (16) and hypophosphorous acid (9).…”

Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition

“…45) 155-156°C), 3e: Yellow prisms (from hexane-CH 2 Cl 2 ), mp 102-104°C (lit. 44) 102-103°C), 3f: Yellow needles (from hexane-CH 2 Cl 2 ), mp 131-133°C (lit. 44) 131-132°C), 3g: Yellow needles (from CHCl 3 ), mp 225-226°C (lit.…”

“…44) 102-103°C), 3f: Yellow needles (from hexane-CH 2 Cl 2 ), mp 131-133°C (lit. 44) 131-132°C), 3g: Yellow needles (from CHCl 3 ), mp 225-226°C (lit. 44) 226°C).…”