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Doctoral Thesis
DOI
10.11606/T.46.1987.tde-22062015-171425
Document
Author
Full name
Ricardo Barros Uchoa
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 1986
Supervisor
Title in Portuguese
Um novo método de obtenção de compostos carbonílicos aromáticos. Aplicação para síntese de benzaldeidos deuterados
Keywords in Portuguese
Compostos aromáticos
Síntese química
Abstract in Portuguese
Esta Tese apresenta duas revisões de literatura: 1. Síntese de aldeídos e cetonas a partir de compostos de enxofre. 2. Síntese de benzaldeídos deuterados. E descrita a reação de sulfenilação de benzil fenil sulfonas, conduzindo a um novo "synthon", α-metiltio-benzil fenil sulfona (1). Y-C6H4-CH(SCH3)SO2C6H5 Y = H,CH3,Cl,OCH3,NO2,CN. É relatada a hidrólise ácida de (1), fornecendo benzaldeídos para substituídos. É proposta a decomposição térmica de (1), como um método novo de síntese de benzaldeídos para substituídos. É descrita uma reação de um passo só, envolvendo alquilação e decomposição térmica de (1) e fornecendo cetonas aromáticas. Este método permite sintetizar cetonas contendo grupos sensíveis a ácidos. O método pirolítico é aplicado à síntese de aldeídos aromáticos deuterados, que são obtidos em 98% de pureza isotópica. Os benzaldeídos deuterados e não deuterados são obtidos em bons rendimentos, não se notando diferenças provenientes do caráter eletrônico dos substituintes no anel. É apresentada uma discussão sobre os aspectos mecanísticos da decomposição térmica.
Title in English
A new method for obtaining aromatic carbonyl compounds. Application to the synthesis of deuterated benzaldehydes
Keywords in English
Aromatic compounds
Chemical synthesis
Abstract in English
This thesis presents two literature reviews: 1. Synthesis of aldehydes and ketones, starting from the sulphur containing compounds 2. Synthesis of deuterated benzaldehydes. The sulphenylation reaction of benzyl phenyl sulphones, leading to a new "synthon", α-methylthio-benzyl phenyl sulphone (1), is described. Y-C6H4-CH(SCH3)SO2C6H5 Y = H,CH3,OCH3,Cl,NO2,CN. Acid hydrolyses of (1) to give p-substituted benzaldehydes are reported. A novel reaction - Thermal Oecomposition of (1) - as an improved method for the synthesis of p-substituted benzaldehydes is proposed. One pot reaction, which consists of alkylation and thermal decomposition of (1), to give aromatic ketones, is reported. Some ketones containing acid-sensitive groups are obtained. The pyrolyt ic method is applied to the synthesis of deuterated aromatic aldehydes, which are obtained in 98% of isotopic purity. The yields of the deuterated and non-deuterated benzaldehydes are good, and do not show any dependence on the eletronic character of the para substituents. A discussion on some mechanistic aspects of the thermal decomposition is presented.
 
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Publishing Date
2015-06-30
 
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