Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents
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 effe...
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| Format: | Article |
| Language: | Arabic |
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Tishreen University
2018-11-01
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| Series: | مجلة جامعة تشرين للبحوث والدراسات العلمية، سلسلة العلوم الأساسية |
| Online Access: | http://journal.tishreen.edu.sy/index.php/bassnc/article/view/4632 |
| Summary: |
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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| ISSN: | 2079-3057 2663-4252 |