Reactions of a novel benzyne annelated with two bicycle [2.2.2]octene units

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4125-4128

  Matsuura, Akira ^a   Nishinaga, Tohru ^a   Komatsu, Koichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BICYCLO[2.2.2]OCTANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIMERIZATION; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 0030998882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00842-3     Document Type: Article

References (20)

1. For a review of benzyne, see Hoffmann, R. W. Dehydrobenzene and Cycloalkynes, Academic Press: New York, 1967.
2. Hart, H.; Lai, C.; Nwokogu, G. C.; Shamouilian, S. Tetrahedron. 1987, 43, 5203 and references cited therein.
3. Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195.
4. Matsuura, A.; Nishinaga, T.; Komatsu, K. Tetrahedron Lett. 1997, 38, in press.
5. Compound 4 was obtained in 75% yield by the coupling of 2-bromobicyclo[2.2.2]oct-2-ene according to the literature method: Vanderesse, R.; Brunet, J. J.; Caubere, P. J. Organomet. Chem. 1984, 264, 263.
6. 2 297.1729, found 297.1716.
7. 34O 506.2610, found 506.2631.
8. Heaney, H. Chem. Rev. 1962, 62, 81. Berry, R. S.; Spokes, G. N.; Stiles, M. J. Am. Chem. Soc. 1962, 84, 3570. Logullo, F. M.; Seitz, A. H.; Friedman, L. Org. Synth. 1968, 48, 12.
9. Heaney, H. Chem. Rev. 1962, 62, 81. Berry, R. S.; Spokes, G. N.; Stiles, M. J. Am. Chem. Soc. 1962, 84, 3570. Logullo, F. M.; Seitz, A. H.; Friedman, L. Org. Synth. 1968, 48, 12.
10. Heaney, H. Chem. Rev. 1962, 62, 81. Berry, R. S.; Spokes, G. N.; Stiles, M. J. Am. Chem. Soc. 1962, 84, 3570. Logullo, F. M.; Seitz, A. H.; Friedman, L. Org. Synth. 1968, 48, 12.
11. 41NO 515.3188, found 515.3207.
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14. +)
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20. Cava, M. P.; Mitchell, M. J. Cyclobutadiene and Related Compounds, Academic Press: New York, 1967; Chapter 10 and 11 and pp 400-411.