Sonochemical synthesis of norbornane derivatives using allene cyclopentadiene Diels-Alder cycloaddition

Tetrahedron Letters

Volumn 39, Issue 30, 1998, Pages 5413-5416

  Raj, C Paul ^a   Dhas, N Arul ^a   Cherkinski, M ^a   Gedanken, A ^a   Braverman, S ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; NORBORNANE DERIVATIVE; SULFOXIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ISOMERISM; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE; ULTRASOUND;

BETULACEAE;

EID: 0032560837     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01016-8     Document Type: Article

References (25)

1. 1. e.g., (a) Winkler, J.D.; Kim, H.S.; Kim, S.; Ando, K.; Houk, K.N. J. Org. Chem. 1997, 62, 2957.
2. (b) Corey, E.J.; Sarshar, S. J. Am. Chem. Soc. 1992, 114, 7938.
3. (c) Raimondi, L.; Brown, F. K.; Gonzalez, J.; Houk, K.N. ibid 1992, 114, 4796.
4. (d) Khan, S.I.; Oliver, J.; Paddon Row, M.N.; Rubin, Y. ibid 1993, 115, 4919.
5. (e) Heathcock, C.H.; Graham, S.; Pirrung, M.C.; Plavee F.; White, C. T. "The Total Synthesis of Natural Products" Apsimon, J. Ed., Wiley, New York, 1983, Vol. 5.
6. 2. Hayakawa, H.; Nishiyama, H.; Kanematsu, K. J. Org. Chem. 1985, 50, 512.
7. (b) Block, E.; Puttnan, F. J. Am. Chem. Soc. 1990, 112, 4072.
8. (c) Padwa, A.; Bullock, W.H.; Norman, B.H. Perumattam, J. J. Org. Chem. 1991, 56, 4252.
9. 3 Braverman, S.; Lior, Z. Tetrahedron Lett. 1994, 35, 6725.
10. 4. Reisse, J.; Caulier, T.; Dickerkheer, C.; Fabre, O., Vandercammen, J.; Delplanke J. L.; Winand, R. Ultrasonics Sonochemistry 1996, 3, 147.
11. (b) Nebols, P.; Bouaziz, Z.; Pillion, H.; Moeini, L.; Piquer, M.J.A.; Luche, J. L.; Riera, A.; Moyano, A.; Pericas, M. A.; Ultrasonics Sonochemistry 1996, 3, 7.
12. (c) Luche J. L. Ultrasonics Sonochemistry 1994, 1, 111.
13. (d) Javed, T.; Mason, T.J.; Phull, S.S.; Baker, N. R. Ultrasonics Sonochemistry 1995, 2, 3.
14. (e) Villacampa, M.; Perez, J.M.; Avendano, C.; Menendez, J.C. Tetrahedron 1994, 50, 10047.
15. (f) Abdulla, R. F. Aldrichimica Acta 1988, 21, 31.
16. (g) Dietmar, P. J. Mater. Chem. 1996, 6, 1605.
17. 5. Suslick, K.S.; Ed. Ultrasound: its Chemical, Physical and Biological Effects, VCH: Weinheim, 1988. Nebois, P.; Bouaziz, P.; Fillion, H.; Moeini, L; Piquer, M.J.A.; Luche, J.L.; Reira, A.; Moyano, A.; Pericas, M.A.; Ultrasonics Sonochemistry 1996 3, 7
18. 5. Suslick, K.S.; Ed. Ultrasound: its Chemical, Physical and Biological Effects, VCH: Weinheim, 1988. Nebois, P.; Bouaziz, P.; Fillion, H.; Moeini, L; Piquer, M.J.A.; Luche, J.L.; Reira, A.; Moyano, A.; Pericas, M.A.; Ultrasonics Sonochemistry 1996 3, 7
19. 6. Braverman, S.; Stabinsky, Y. Isr. J. Chem. 1967, 5, 125. See also Braverman, S. in The Chemistry of Sulfones and Sulfoxides, Ed. Patai, S.; Rappoport, Z.; Stirling, C.J.M. John Willey & Sons, Chichester, 1988, Ch. 14.
20. 6. Braverman, S.; Stabinsky, Y. Isr. J. Chem. 1967, 5, 125. See also Braverman, S. in The Chemistry of Sulfones and Sulfoxides, Ed. Patai, S.; Rappoport, Z.; Stirling, C.J.M. John Willey & Sons, Chichester, 1988, Ch. 14.
21. 3), 110.06(C-8), 135.21 (C-6), 140.22(C-5), 147.40 (C-3).
22. 8. (a) Hopf, H. In The Chemistry of Allenes, Landor, S.R. Ed., vol. 2. Academic Press, London, 1982, Ch. 4.2.
23. (b) Braverman, S. in The Chemistry of Double Bonded Functional Groups - Supplement A2, Patai, S.; Rappoport, Z. Eds. John Wiley, New York, 1990, Ch.14.
24. 9 Caulier, T. P.; Reisse, J. J. Org. Chem. 1996, 61, 2547
25. 3 by surface reaction with the chloro groups on the reagents. The possibility (though remote) of some form of catalysis by such materials was removed by preliminary sonification of the allene in the absence of cyclopentadiene, followed by conventional reaction of the pre-sonicated material with added cyclopentadiene. We thank the referee for the suggestion of this control experiment.