An Ethylene and Terminal Olefin Equivalent in [4 + 2] π Cycloadditions. General Synthetic Application of Phenyl Vinyl Sulfone to the Construction of Functionalized Six-Membered Rings

Journal of the American Chemical Society

Volumn 102, Issue 2, 1980, Pages 853-855

  Carr, Richard V C ^a   Paquette, Leo A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000247517     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00522a075     Document Type: Article

References (26)

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4. The more strained nature of the norbornene double bond causes molecules of this ilk to be more reactive: (a) Alder, K.; Stein, G.; Finzehagen, H. Justus Liebigs Ann. Chem. 1931, 485, 223-246.
5. Alder, K.; Stein, G.; Reese, J.; Grassmann, W. Justus Liebigs Ann. Chem. 1932, 496, 204-251.
6. Dienophlles of exceptionally high reactivity are known to facilitate cycloaddition to unactlvated olefins. See, for example, Eaton, P. E.; Chakraborty, U. R. J. Am. Chem. Soc. 1978, 100, 3634-3635.
7. Acetylene Is deserving of similar classification: Paquette, L. A.; Moerck, R. E.; Harlrchian, B.; Magnus, P. D. J. Am. Chem. Soc. 1978, 100, 1597-1599.
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24. The phenyl sulfonyl group does not exert marked shielding effects on proximate aryl protons, much like a halogen atom. In this connection, the three-proton aromatic pattern in 27 (the phenyl group discounted) compares very closely with that of 3-bromo-o-xylene (Aldrich Library, spectrum 4-59A) and differs substantially from that of 4-bromo-o-xylene (Aldrich Library, spectrum 4-60B). The remainder of the spectrum bears many similarities to that exhibited by benzopmane: Paquette, L. A.; Melega, W. P.; Kramer, J. D. Tetrahedron Lett. 1976, 4033.
25. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3857-3860.
26. This work was supported by the National Science Foundation whom we thank.