Cyclobutenes by platinum-catalyzed cycloisomerization reactions of enynes

Journal of the American Chemical Society

Volumn 127, Issue 23, 2005, Pages 8244-8245

  Fürstner, Alois ^a   Davies, Paul W ^a   Gress, Tobias ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; CYCLOPROPANE DERIVATIVE; PLATINUM;

ARTICLE; CANONICAL ANALYSIS; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 20444496467     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050845g     Document Type: Article

References (29)

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19. Single examples of cyclobutenes were reported in ref 6b and the following: Bajracharya, G. B.; Nakamura, I.; Yamamoto, Y. J. Org. Chem. 2005, 70, 892. In both cases, the position of the double bond differs from that in compound 2 and its analogues.
20. Lutton, J. M.; Parry, R. W. J. Am. Chem. Soc. 1954, 76, 4271.
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22. Only enynes with ether substituents on their phenyl rings show this characteristic coloration of the reaction mixture.
23. In addition, coordination of Pt(+2) in intermediate F to CO reduces its electron density and, hence, its ability to eliminate directly, thus rendering proton loss a competitive process.
24. A similar argument pertains to products 7 and 9, which are significantly more stable than their positional isomers.
25. Cyclobutenes with the double bond in the same location are extremely scarce; two examples are described as products of palladol-catalyzed processes: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636.
26. (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647.
27. While this paper was under review, Echavarren et al. reported two related examples using gold complexes as catalysts: Nieto-Oberhuber, C.; López, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178.
28. Metallacyclopentenes were proposed as intermediates in cycloisomerizations of electron-poor enynes mediated by palladacycle catalysts: (a) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850.
29. (b) Trost, B. M.; Yanai, M.; Hoogsteen, K. J. Am. Chem. Soc. 1993, 115, 5294.