Novel tocopherol compounds I. Bromination of α-tocopherol — reaction mechanism and synthetic applications
Bromination of α-tocopherol is shown to proceed as a two-step process including the occurrence of an ortho-quinone methide, not as a radical-chain reaction, contrary to earlier reports. The ortho-quinone methide intermediate is also produced by oxidation of a-tocopherol with silver oxide and can be...
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| Published in: | Tetrahedron Vol. 51; no. 29; pp. 7919 - 7926 |
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| Main Authors: | , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Elsevier Ltd
17-07-1995
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| Online Access: | Get full text |
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| Summary: | Bromination of α-tocopherol is shown to proceed as a two-step process including the occurrence of an ortho-quinone methide, not as a radical-chain reaction, contrary to earlier reports. The ortho-quinone methide intermediate is also produced by oxidation of a-tocopherol with silver oxide and can be trapped in the presence of electron-rich dienophiles in a hetero-Diels-Alder reaction to form novel dichromanes in high yields. |
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| ISSN: | 0040-4020 1464-5416 |
| DOI: | 10.1016/0040-4020(95)00421-4 |