2-(tert-Butyl)-4-phenyloxetane
The two geometric isomers of 2-(tert-butyl)-4-phenyloxetane have, for the first time, been prepared starting from the commercially available 4,4-dimethyl-1-phenylpentane-1,3-dione. The latter was reduced with NaBH4 to give a mixture of diastereomeric syn and anti diols which were then stereospecific...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2017-02-01
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| Series: | Molbank |
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| Online Access: | http://www.mdpi.com/1422-8599/2017/1/M930 |
| _version_ | 1818453350240223232 |
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| author | Filippo Maria Perna Paola Vitale Simona Summa Vito Capriati |
| author_facet | Filippo Maria Perna Paola Vitale Simona Summa Vito Capriati |
| author_sort | Filippo Maria Perna |
| collection | DOAJ |
| description | The two geometric isomers of 2-(tert-butyl)-4-phenyloxetane have, for the first time, been prepared starting from the commercially available 4,4-dimethyl-1-phenylpentane-1,3-dione. The latter was reduced with NaBH4 to give a mixture of diastereomeric syn and anti diols which were then stereospecifically cyclized into the corresponding oxetanes with an overall yield for the two steps of 69.6%. The newly synthesized stereoisomeric four-membered oxygenated heterocycles were separated by column chromatography on silica gel and fully spectroscopically characterized. |
| first_indexed | 2024-12-14T21:37:35Z |
| format | Article |
| id | doaj.art-ab68c31fd79748d4803e4417420f0218 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-12-14T21:37:35Z |
| publishDate | 2017-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-ab68c31fd79748d4803e4417420f02182022-12-21T22:46:33ZengMDPI AGMolbank1422-85992017-02-0120171M93010.3390/M930M9302-(tert-Butyl)-4-phenyloxetaneFilippo Maria Perna0Paola Vitale1Simona Summa2Vito Capriati3Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari “A. Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyDipartimento di Farmacia-Scienze del Farmaco, Università di Bari “A. Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyDipartimento di Farmacia-Scienze del Farmaco, Università di Bari “A. Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyDipartimento di Farmacia-Scienze del Farmaco, Università di Bari “A. Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyThe two geometric isomers of 2-(tert-butyl)-4-phenyloxetane have, for the first time, been prepared starting from the commercially available 4,4-dimethyl-1-phenylpentane-1,3-dione. The latter was reduced with NaBH4 to give a mixture of diastereomeric syn and anti diols which were then stereospecifically cyclized into the corresponding oxetanes with an overall yield for the two steps of 69.6%. The newly synthesized stereoisomeric four-membered oxygenated heterocycles were separated by column chromatography on silica gel and fully spectroscopically characterized.http://www.mdpi.com/1422-8599/2017/1/M930oxetanesdiolsdiastereoisomerscyclization reactionsNMRheterocycles |
| spellingShingle | Filippo Maria Perna Paola Vitale Simona Summa Vito Capriati 2-(tert-Butyl)-4-phenyloxetane Molbank oxetanes diols diastereoisomers cyclization reactions NMR heterocycles |
| title | 2-(tert-Butyl)-4-phenyloxetane |
| title_full | 2-(tert-Butyl)-4-phenyloxetane |
| title_fullStr | 2-(tert-Butyl)-4-phenyloxetane |
| title_full_unstemmed | 2-(tert-Butyl)-4-phenyloxetane |
| title_short | 2-(tert-Butyl)-4-phenyloxetane |
| title_sort | 2 tert butyl 4 phenyloxetane |
| topic | oxetanes diols diastereoisomers cyclization reactions NMR heterocycles |
| url | http://www.mdpi.com/1422-8599/2017/1/M930 |
| work_keys_str_mv | AT filippomariaperna 2tertbutyl4phenyloxetane AT paolavitale 2tertbutyl4phenyloxetane AT simonasumma 2tertbutyl4phenyloxetane AT vitocapriati 2tertbutyl4phenyloxetane |