Reaction of Acyl Chlorides with In Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran
Attempting to apply the in situ production of PhSeZnSePh to the synthesis of selenoesters, an unexpected reaction involving the solvent (tetrahydrofuran) was observed and studied. We reported here some evidences about the mechanism and the possibility to control the chemoselectivity of this new reac...
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| Format: | Article |
| Language: | English |
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Wiley
2016-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2016/2849140 |
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| author | Gemma Bellino Marialaura Scisciani Jaqueline Pinto Vargas Luca Sancineto Luana Bagnoli Francesca Marini Diogo Seibert Lüdtke Eder Joao Lenardao Claudio Santi |
| author_facet | Gemma Bellino Marialaura Scisciani Jaqueline Pinto Vargas Luca Sancineto Luana Bagnoli Francesca Marini Diogo Seibert Lüdtke Eder Joao Lenardao Claudio Santi |
| author_sort | Gemma Bellino |
| collection | DOAJ |
| description | Attempting to apply the in situ production of PhSeZnSePh to the synthesis of selenoesters, an unexpected reaction involving the solvent (tetrahydrofuran) was observed and studied. We reported here some evidences about the mechanism and the possibility to control the chemoselectivity of this new reaction that afforded the formation of interesting selenoderivatives in which the selenium moiety and the carboxylic one are spaced by four carbon units. |
| format | Article |
| id | doaj-art-f8dde6489ef34739950e0ce4bf8a11f4 |
| institution | DOAJ |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2016-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-f8dde6489ef34739950e0ce4bf8a11f42025-08-20T03:20:05ZengWileyJournal of Chemistry2090-90632090-90712016-01-01201610.1155/2016/28491402849140Reaction of Acyl Chlorides with In Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of TetrahydrofuranGemma Bellino0Marialaura Scisciani1Jaqueline Pinto Vargas2Luca Sancineto3Luana Bagnoli4Francesca Marini5Diogo Seibert Lüdtke6Eder Joao Lenardao7Claudio Santi8Group of Catalysis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06100 Perugia, ItalyGroup of Catalysis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06100 Perugia, ItalyInstituto de Química, Universidade Federal do Rio Grande do Sul (UFRGS), Avenida Bento Gonçalves 9500, 91501-970 Porto Alegre, RS, BrazilGroup of Catalysis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06100 Perugia, ItalyGroup of Catalysis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06100 Perugia, ItalyGroup of Catalysis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06100 Perugia, ItalyInstituto de Química, Universidade Federal do Rio Grande do Sul (UFRGS), Avenida Bento Gonçalves 9500, 91501-970 Porto Alegre, RS, BrazilLaboratório de Síntese Orgânica Limpa (LASOL), Centro de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, BrazilGroup of Catalysis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06100 Perugia, ItalyAttempting to apply the in situ production of PhSeZnSePh to the synthesis of selenoesters, an unexpected reaction involving the solvent (tetrahydrofuran) was observed and studied. We reported here some evidences about the mechanism and the possibility to control the chemoselectivity of this new reaction that afforded the formation of interesting selenoderivatives in which the selenium moiety and the carboxylic one are spaced by four carbon units.http://dx.doi.org/10.1155/2016/2849140 |
| spellingShingle | Gemma Bellino Marialaura Scisciani Jaqueline Pinto Vargas Luca Sancineto Luana Bagnoli Francesca Marini Diogo Seibert Lüdtke Eder Joao Lenardao Claudio Santi Reaction of Acyl Chlorides with In Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran Journal of Chemistry |
| title | Reaction of Acyl Chlorides with In Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran |
| title_full | Reaction of Acyl Chlorides with In Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran |
| title_fullStr | Reaction of Acyl Chlorides with In Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran |
| title_full_unstemmed | Reaction of Acyl Chlorides with In Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran |
| title_short | Reaction of Acyl Chlorides with In Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran |
| title_sort | reaction of acyl chlorides with in situ formed zinc selenolates synthesis of selenoesters versus ring opening reaction of tetrahydrofuran |
| url | http://dx.doi.org/10.1155/2016/2849140 |
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