Palladium-Catalyzed 1,4-Acetoxy-Trifluoroacetoxylation and 1,4-Alkoxy-Trifluoroacetoxylation of Cyclic 1,3-Dienes. Scope and Mechanism

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2523-2529

  Aranyos, Attila ^a   Szabó, Kálmán J ^a,b   Bäckvall, Jan E ^a,b  

^a UPPSALA UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001482398     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971738a     Document Type: Article

References (56)

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34. 2/cat. BQ was developed in our laboratory in 1983: Bäckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Bäckvall, J. E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
35. 11
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37. In all these compounds there are two conformations the boat and the chair, which have about the same energy. As the β-substituent effect is stronger in the chair conformation than in the boat one, only the former was considered here. For the different conformers of similar compounds see ref 12.
38. In the case of the acetate and trifluoroacetate, protonation at the carbonyl oxygen is energetically more favorable. However, protonation of O4 allows direct comparison with the methoxy group. See ref 12c.
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41. In the sense of the cleavage reaction.
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