New Insight into the Reactivity of S,S-Bis-ylide
The present work focuses on the reactivity of S,S-bis-ylide <b>2</b>, which presents a strong nucleophilic character, as evidenced by reactions with methyl iodide and CO<sub>2</sub>, affording C-methylated salts <b>3</b> and betaine <b>4</b>, respectiv...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/8/3295 |
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| author | Ugo Authesserre V. S. V. S. N. Swamy Nathalie Saffon-Merceron Antoine Baceiredo Tsuyoshi Kato Eddy Maerten |
| author_facet | Ugo Authesserre V. S. V. S. N. Swamy Nathalie Saffon-Merceron Antoine Baceiredo Tsuyoshi Kato Eddy Maerten |
| author_sort | Ugo Authesserre |
| collection | DOAJ |
| description | The present work focuses on the reactivity of S,S-bis-ylide <b>2</b>, which presents a strong nucleophilic character, as evidenced by reactions with methyl iodide and CO<sub>2</sub>, affording C-methylated salts <b>3</b> and betaine <b>4</b>, respectively. The derivatization of betaine <b>4</b> affords the corresponding ester derivative <b>6</b>, which is fully characterized by using NMR spectroscopy and X-ray diffraction analysis. Furthermore, an original reaction with phosphenium ions leads to the formation of a transient push–pull phosphino(sulfonio)carbene <b>8</b>, which rearranges to give stabilized sulfonium ylide derivative <b>7</b>. |
| first_indexed | 2024-03-11T04:42:59Z |
| format | Article |
| id | doaj.art-e726ac848cd64ffd83934624616528c7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T04:42:59Z |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e726ac848cd64ffd83934624616528c72023-11-17T20:36:55ZengMDPI AGMolecules1420-30492023-04-01288329510.3390/molecules28083295New Insight into the Reactivity of S,S-Bis-ylideUgo Authesserre0V. S. V. S. N. Swamy1Nathalie Saffon-Merceron2Antoine Baceiredo3Tsuyoshi Kato4Eddy Maerten5Université de Toulouse, UPS, and CNRS, LHFA UMR 5069, 118 Route de Narbonne, 31062 Toulouse, FranceUniversité de Toulouse, UPS, and CNRS, LHFA UMR 5069, 118 Route de Narbonne, 31062 Toulouse, FranceUniversité de Toulouse, UPS, and CNRS, ICT UAR2599 118 Route de Narbonne, 31062 Toulouse, FranceUniversité de Toulouse, UPS, and CNRS, LHFA UMR 5069, 118 Route de Narbonne, 31062 Toulouse, FranceUniversité de Toulouse, UPS, and CNRS, LHFA UMR 5069, 118 Route de Narbonne, 31062 Toulouse, FranceUniversité de Toulouse, UPS, and CNRS, LHFA UMR 5069, 118 Route de Narbonne, 31062 Toulouse, FranceThe present work focuses on the reactivity of S,S-bis-ylide <b>2</b>, which presents a strong nucleophilic character, as evidenced by reactions with methyl iodide and CO<sub>2</sub>, affording C-methylated salts <b>3</b> and betaine <b>4</b>, respectively. The derivatization of betaine <b>4</b> affords the corresponding ester derivative <b>6</b>, which is fully characterized by using NMR spectroscopy and X-ray diffraction analysis. Furthermore, an original reaction with phosphenium ions leads to the formation of a transient push–pull phosphino(sulfonio)carbene <b>8</b>, which rearranges to give stabilized sulfonium ylide derivative <b>7</b>.https://www.mdpi.com/1420-3049/28/8/3295bis-ylidesylidecarbonephospheniumcarbenecarbon dioxide |
| spellingShingle | Ugo Authesserre V. S. V. S. N. Swamy Nathalie Saffon-Merceron Antoine Baceiredo Tsuyoshi Kato Eddy Maerten New Insight into the Reactivity of S,S-Bis-ylide Molecules bis-ylides ylide carbone phosphenium carbene carbon dioxide |
| title | New Insight into the Reactivity of S,S-Bis-ylide |
| title_full | New Insight into the Reactivity of S,S-Bis-ylide |
| title_fullStr | New Insight into the Reactivity of S,S-Bis-ylide |
| title_full_unstemmed | New Insight into the Reactivity of S,S-Bis-ylide |
| title_short | New Insight into the Reactivity of S,S-Bis-ylide |
| title_sort | new insight into the reactivity of s s bis ylide |
| topic | bis-ylides ylide carbone phosphenium carbene carbon dioxide |
| url | https://www.mdpi.com/1420-3049/28/8/3295 |
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