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Master's Dissertation
DOI
10.11606/D.46.2000.tde-04122014-113343
Document
Author
Full name
Eduardo Kunio Chinone Yoshikawa
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2000
Supervisor
Committee
Marzorati, Liliana (President)
Brocksom, Ursula
Gruber, Jonas
Title in Portuguese
Estudos da Decomposição Térmica de Alguns Sulfóxidos -Funcionalizados
Keywords in Portuguese
Compostos de enxofre
Decomposicao térmica
Química orgânica
Sulfoxidos
Abstract in Portuguese
A decomposição térmica dos compostos sulfoxídicos (1)-(4) foi efetuada a ca. 140 °C, até conversão total do material de partida. A mistura de produtos resultante, em cada caso, foi analisada por cromatografia gasosa/espectrometria de massas. Foram preparadas amostras autênticas dos compostos assim identificados e, no caso dos sulfóxidos (2)-(4), a composição do produto de termólise foi determinada através de análises por cromatografia gasosa e RMN de 1H, utilizando-se o método do padrão interno. Os resultados obtidos estão sumarizados abaixo: Tabela - ver arquivo em PDF - Para três dos substratos estudados, os produtos finais poderiam originar-se de hemitiocetais intermediários, formados por um rearranjo de Pummerer. Este mecanismo de decomposição parece ser geral para sulfóxidos β-carbonílicos. No entanto, o substrato (1) decompõe-se termicamente por mecanismo radicalar.
Title in English
Studies of thermal decomposition of some α- functionalized sulfoxides
Keywords in English
Organic chemistry
Sulfoxides
Sulfur compounds
Thermal decomposition
Abstract in English
The thermal decomposition of sulfoxides (1)-(4) was performed at ca. 140 °C, until complete consumption of the starting materiais. In each case, the product mixture was analyzed by GC/MS. Authentic samples of identified components were prepared, and in the case of sulfoxides (2)-(4), the crude product composition was determinded by gas chromatography and 1H NMR analyses (internal standard method).Results are as follows: See chart PDF file - For three cases, final products could originate from intermediate hemithioacetals, generated via a thermal Pummerer rearrangement. lhis decomposition mechanism seems to be general for the thermolysis of β-carbonyl sulfoxides. However, sulfoxide (1) decomposes under heating via a radical mechanism.
 
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Publishing Date
2014-12-04
 
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