Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents

Authors

  • abdel karim Al-Hamad

Abstract

 

Organosulfur compounds have been exploited to reverse the reactivity of carbonyl compounds. The heteroatom  produces a  reactivity pattern in a carbon skeleton. Its electronegativity, being greater than that of carbon (-I effect) and its ability to stabilize an adjacent positive charge (+M effect) makes the sites susceptible to be attacked by reagents possessing a given “philicity”.

Nucleophiles attacks the odd C atomes ( attack) whereas electrophiles attacks the even C atomes (attack) of the carbonyl compounds. If the reactivity of a carbonyl could be reversed, the acyl carbon would become nucleophilic, and if this transformation can be accomplished, the carbonyl should be  regenerated. Seebach termed this process  ''umpolung''.

 

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Published

2018-11-14

How to Cite

1.
Al-Hamad abdel karim. Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents. TUJ-BA [Internet]. 2018Nov.14 [cited 2024Nov.24];40(5). Available from: https://journal.tishreen.edu.sy/index.php/bassnc/article/view/4632

Issue

Vol. 40 No. 5 (2018): العلوم الأساسية

Section

Articles

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