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 |
| _version_ | 1797418051428155392 |
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| author | عبد الكريم الحمد |
| author_facet | عبد الكريم الحمد |
| author_sort | عبد الكريم الحمد |
| collection | DOAJ |
| description |
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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| first_indexed | 2024-03-09T06:26:56Z |
| format | Article |
| id | doaj.art-7467e4ed6b274f11b57e1909573e9728 |
| institution | Directory Open Access Journal |
| issn | 2079-3057 2663-4252 |
| language | Arabic |
| last_indexed | 2024-03-09T06:26:56Z |
| publishDate | 2018-11-01 |
| publisher | Tishreen University |
| record_format | Article |
| series | مجلة جامعة تشرين للبحوث والدراسات العلمية، سلسلة العلوم الأساسية |
| spelling | doaj.art-7467e4ed6b274f11b57e1909573e97282023-12-03T11:18:27ZaraTishreen Universityمجلة جامعة تشرين للبحوث والدراسات العلمية، سلسلة العلوم الأساسية2079-30572663-42522018-11-01405Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagentsعبد الكريم الحمد 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''. http://journal.tishreen.edu.sy/index.php/bassnc/article/view/4632 |
| spellingShingle | عبد الكريم الحمد Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents مجلة جامعة تشرين للبحوث والدراسات العلمية، سلسلة العلوم الأساسية |
| title | Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents |
| title_full | Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents |
| title_fullStr | Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents |
| title_full_unstemmed | Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents |
| title_short | Inversion of Reactivity (umpolung) of Carbonyl Compounds Using Organosulfur Compounds Reagents |
| title_sort | inversion of reactivity umpolung of carbonyl compounds using organosulfur compounds reagents |
| url | http://journal.tishreen.edu.sy/index.php/bassnc/article/view/4632 |
| work_keys_str_mv | AT ʿbdạlkrymạlḥmd inversionofreactivityumpolungofcarbonylcompoundsusingorganosulfurcompoundsreagents |