Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins
Unlike endocyc1ic olefins the major product from the SeO,/H,O, oxidation of exocyc1ic olefins is the same ally1ic alcohol as from the uncata1ysed oxidation. Minor products derived from epoxide intermediates were investigated. The use of SeO, as an allylic oxidant for oJefins has been extensively inv...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
1976
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| Online Access: | http://psasir.upm.edu.my/id/eprint/33878/1/12.%2033878%20diterpene%20chemistry.pdf |
| _version_ | 1796972398854012928 |
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| author | Francis, M. J. Grant, P. K. Low, K. S. Weavers, R. T. |
| author_facet | Francis, M. J. Grant, P. K. Low, K. S. Weavers, R. T. |
| author_sort | Francis, M. J. |
| collection | UPM |
| description | Unlike endocyc1ic olefins the major product from the SeO,/H,O, oxidation of exocyc1ic olefins is the same ally1ic alcohol as from the uncata1ysed oxidation. Minor products derived from epoxide intermediates were investigated. The use of SeO, as an allylic oxidant for oJefins has been extensively investigated, the functionality of the product being to a degree solvent dependent. Although the earlier mechanism of Guillemonat' is incorrect, his rules for the prediction of the position of oxidation still remain valid. A survey by Tratchenburg' of the current position in SeO, oxidation postulates allylic oxidation as proceeding through the intermediacy of an oxaselenocyclobutane to a selemte ester which IS solvated by competitive unimolecular (SN 1) and bimolecular (SN2') processes (Scheme I). |
| first_indexed | 2024-03-06T08:27:26Z |
| format | Article |
| id | upm.eprints-33878 |
| institution | Universiti Putra Malaysia |
| language | English |
| last_indexed | 2024-03-06T08:27:26Z |
| publishDate | 1976 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | upm.eprints-338782015-04-21T04:44:01Z http://psasir.upm.edu.my/id/eprint/33878/ Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins Francis, M. J. Grant, P. K. Low, K. S. Weavers, R. T. Unlike endocyc1ic olefins the major product from the SeO,/H,O, oxidation of exocyc1ic olefins is the same ally1ic alcohol as from the uncata1ysed oxidation. Minor products derived from epoxide intermediates were investigated. The use of SeO, as an allylic oxidant for oJefins has been extensively investigated, the functionality of the product being to a degree solvent dependent. Although the earlier mechanism of Guillemonat' is incorrect, his rules for the prediction of the position of oxidation still remain valid. A survey by Tratchenburg' of the current position in SeO, oxidation postulates allylic oxidation as proceeding through the intermediacy of an oxaselenocyclobutane to a selemte ester which IS solvated by competitive unimolecular (SN 1) and bimolecular (SN2') processes (Scheme I). Elsevier 1976 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/33878/1/12.%2033878%20diterpene%20chemistry.pdf Francis, M. J. and Grant, P. K. and Low, K. S. and Weavers, R. T. (1976) Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins. Tetrahedron, 32 (1). pp. 95-101. ISSN 0040-4020 10.1016/0040-4020(76)80026-9 |
| spellingShingle | Francis, M. J. Grant, P. K. Low, K. S. Weavers, R. T. Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins |
| title | Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins |
| title_full | Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins |
| title_fullStr | Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins |
| title_full_unstemmed | Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins |
| title_short | Diterpene chemistry—VI: SeO2/H2O2 oxidations of exocyclic olefins |
| title_sort | diterpene chemistry vi seo2 h2o2 oxidations of exocyclic olefins |
| url | http://psasir.upm.edu.my/id/eprint/33878/1/12.%2033878%20diterpene%20chemistry.pdf |
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