Acid-catalyzed rearrangement of aryl-substituted homobenzoquinone epoxides

Organic Letters

Volumn 9, Issue 17, 2007, Pages 3421-3424

  Asahara, H ^a   Kubo, E ^a   Togaya, K ^a   Koizumi, T ^a   Mochizuki, E ^a   Oshima, T ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548167555     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7014576     Document Type: Article

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25. Details will be described elsewhere.
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30. 1H NMR, even for shorter reaction times (10 min, 30% conversion) of 1i under the same conditions. Another possibility that compound 1g undergoes a prior acyl migration coupled with cyclopropane ring cleavage to give an intermediary dioxocycloheptene epoxide is unlikely, because of its increased heat of formation (by 70.79 kJ/mol on DFT calculation with B3LYP/6-31G*). Incidentally, 2g and 3 are more stable than 1g by 76.94 and 80.35 kJ/mol, respectively.
31. Crystallographic data for the structures of 2f, 4, and 5 have been deposited with the Cambridge Crystallographic Data Center as supplementary publication numbers CCDC 650017, 650018, and 650209. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 IEZ, U.K. Fax: +44-1233-336033. E-mail: deposit@ccdc.cam.ac.uk.
32. 3 for 12 h under the same conditions provided compound 5 in 96% yield on 52% conversion.
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