Synthesis of Hydroxy(or Hydroperoxy)-Substituted 1,2,4-Trioxacycloalkanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals
Ozonolyses of unsaturated hydroperoxy acetals 4a−k gave in each case the mixtures of products containing the corresponding trioxanes 8a−f and 12e,f, trioxepanes 12g−i, trioxocane 12j, and trioxonane 12k. By choosing the proper conditions of the ozonolysis, the desired cyclic peroxide was selectively...
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| Published in: | Journal of organic chemistry Vol. 62; no. 15; pp. 4949 - 4954 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
American Chemical Society
25-07-1997
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| Online Access: | Get full text |
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| Summary: | Ozonolyses of unsaturated hydroperoxy acetals 4a−k gave in each case the mixtures of products containing the corresponding trioxanes 8a−f and 12e,f, trioxepanes 12g−i, trioxocane 12j, and trioxonane 12k. By choosing the proper conditions of the ozonolysis, the desired cyclic peroxide was selectively obtained in moderate to good yield. Alternatively, acid-catalyzed cyclization of the methanol-derived ozonolysis products 13h and 13j provided the corresponding trioxepane 12h and trioxocane 12j, respectively. |
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| Bibliography: | Abstract published in Advance ACS Abstracts, July 15, 1997. istex:976C550F2E230FC6CA5FD576411CB7D639779935 ark:/67375/TPS-J8313RDT-C |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/jo970555l |