Diels-Alder Reactions of Tetraethynylcyclopentadienones. An Approach to Differentially Substituted Hexaethynylbenzenes of C2v Symmetry

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3430-3431

  Tobe, Yoshito ^a   Kubota, Kouzoh ^a   Naemura, Koichiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000444253     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970309+     Document Type: Article

References (36)

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11. 3h symmetry were synthesized by Prof. Y. Rubin's group at UCLA: Anthony, J. E.; Khan, S. I.; Rubin, Y. Tetrahedron Lett., in press.
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14. (a) This work was reported at the 70th Annual Meeting of the Chemical Society of Japan (March 28-31, 1996): Abstracts of Papers, 2H141.
15. (b) However, we became aware at the 1995 International Chemical Congress of Pacific Basin Societies (Dec 17-22, 1995) that a similar approach had been undertaken independently by Prof. Rubin: Abstract of Papers, ORGN 0650.
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17. We expected that dienone 2 would serve as a precursor to the pentaethynylcyclopentadienyl system (see ref 9c) as well as tetraethynyl-substituted cyclobutadiene and tetrahedrane. For transition metal complexes of pentaethynylcyclopentadienyl and tetraethynylcyclobutadiene derivatives, see: (a) Bunz, U. H. F.; Enkelmann, V.; Räder, J. Organometallics 1993, 12, 4745. (b) Bunz, U. H. F.; Wiegelmann-Kreiter, J. E. C. Chem. Ber. 1996, 129, 785.
18. We expected that dienone 2 would serve as a precursor to the pentaethynylcyclopentadienyl system (see ref 9c) as well as tetraethynyl-substituted cyclobutadiene and tetrahedrane. For transition metal complexes of pentaethynylcyclopentadienyl and tetraethynylcyclobutadiene derivatives, see: (a) Bunz, U. H. F.; Enkelmann, V.; Räder, J. Organometallics 1993, 12, 4745. (b) Bunz, U. H. F.; Wiegelmann-Kreiter, J. E. C. Chem. Ber. 1996, 129, 785.
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36. The formation of 14 can be explained in terms of intramolecular addition of a carbenoid to the neighboring double bond and subsequent cleavage of the strained cyclopropane bond.