Intermolecular [4 + 2] cycloaddition of o-quinodimethanes derived from ene-bis(sulfinylallenes)

Journal of Organic Chemistry

Volumn 71, Issue 18, 2006, Pages 6908-6914

  Kitagaki, Shinji ^a   Katoh, Kumiko ^a   Ohdachi, Kazuhiro ^a   Takahashi, Yuji ^a   Shibata, Daisuke ^a   Mukai, Chisato ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AROMATIC COMPOUNDS; METHANE; MOLECULAR DYNAMICS; OLEFINS; REACTION KINETICS;

BIS(PROPARGYL ALCOHOLS); CYCLOADDITION; CYCLOADUCTS; HETEROCYCLES;

ADDITION REACTIONS;

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALLENE DERIVATIVE; BENZENE DERIVATIVE; BRIDGED COMPOUND; ETHYLENE; METHANE; QUINONE DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; CYCLOADDITION; DIASTEREOISOMER; ELECTRON TRANSPORT; MOLECULAR INTERACTION; QUANTUM YIELD; REACTION ANALYSIS; SONOGASHIRA REACTION; TEMPERATURE DEPENDENCE;

CHEMISTRY, ORGANIC; METHANE; POLYCYCLIC HYDROCARBONS, AROMATIC; QUINONES; SULFUR COMPOUNDS;

EID: 33748692851     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061014b     Document Type: Article

References (44)

1. (a) Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779-4807.
2. (b) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
3. (c) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667.
4. (d) Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction: Selected Practical Methods; John Wiley & Sons: Chichester, West Sussex, 2002.
5. (a) Segura, J. L.; Martin, N. Chem. Rev. 1999, 99, 3199-3246.
6. (b) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Int. 1991, 23, 237-272.
7. (c) Charlton, J. L. Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889.
8. (d) Oppolzer, W. Synthesis 1978, 793-802.
9. (a) Tanaka, K.; Takamoto, N.; Tezuka, Y.; Kato, M.; Toda, F. Tetrahedron 2001, 57, 3761-3767.
10. (b) Toda, F.; Tanaka, K.; Sano, I.; Isozaki, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1757-1758.
11. (c) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369-375.
12. (d) Inanaga, J.; Sugimoto, Y.; Hanamoto, T. Tetrahedron Lett. 1992, 33, 7035-7038.
13. (e) Ezcurra, J. E.; Moore, H. W. Tetrahedron Lett. 1993, 34, 6177-6180.
14. (f) Braverman, S.; Duar, Y. J. Am. Chem. Soc. 1990, 112, 5830-5837.
15. (g) Höhn, J.; Weyerstahl, P. Chem. Ber. 1983, 116, 808-814.
16. (h) Staab, H. A.; Draeger, B. Chem. Ber. 1972, 105, 2320-2333.
17. (i) Bowes, C. M.; Montecalvo, D. F.; Sondheimer, F. Tetrahedron Lett. 1973, 3181-3184.
18. (j) Ben-Efraim, D. A.; Sondheimer, F. Tetrahedron Lett. 1963, 313-315.
19. Kitagaki, S.; Ohdachi, K.; Katoh, K.; Mukai, C. Org. Lett. 2006, 8, 95-98.
20. Homer, L.; Binder, V. Liebigs Ann. Chem. 1972, 757, 33-68.
21. The tandem formation and intramolecular [4 + 2] cycloaddition of 1-sulfinyl-1-vinylallenes, triggered by [2,3]-sigmatropic rearrangement of the corresponding propargyl sulfenates, have been reported: (a) Okamura, W. H.; Curtin, M. L. Synlett 1990, 1-9.
22. (b) Curtin, M. L.; Okamura, W. H. J. Org. Chem. 1990, 55, 5278-5287.
23. (c) Gibbs, R. A.; Bartels, K.; Lee, R. W. K.; Okamura, W. H. J. Am. Chem. Soc. 1989, 111, 3717-3725.
24. (d) Gibbs, R. A.; Okamura, W. H. J. Am. Chem. Soc. 1988, 110, 4062-4063.
25. The intermolecular cycloaddition reaction of the o-quinodimethane derived from cis-4-octene-2,6-diyne-1,8-diol and PhSCl was described in the review article by Grissom (Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518). However, no original manuscript dealing with the details of this reaction is available.
26. Basak, A.; Shain, J. C.; Khamrai, U. K.; Rudra, K. R.; Basak, A. J. Chem. Soc., Perkin Trans. 1 2000, 1955-1964.
27. 2.
28. For the low reactivity of maleate esters for dienes, see: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2072-2085 and references therein.
29. There are some examples where cycloadditions of o-quinodimethanes with maleate esters give mixtures of cis- and trans-cycloadducts due to the isomerization of maleates prior to the cycloaddition process occurring: (a) Reference 10.
30. (b) Inaba, S.; Wehmeyer, R. M.; Forkner, M. W.; Rieke, R. D. J. Org. Chem. 1988, 53, 339-344. See also ref 3c.
31. Mladenova, M.; Alami, M.; Linstramelle, G. Synth. Commun. 1996, 26, 2831-2842.
32. PhSCl was prepared by a literature procedure and stored in the freezer: Barrett, A. G. M.; Dhanak, D.; Graboski, G. G.; Taylor, S. J. Org. Synth. 1990, 68, 8-12.
33. Davies, M. J.; Hawkins, C. L. Free Radic. Res. 2000, 33, 719-729.
34. King, A. O.; Negishi, E.; Villani, F. J., Jr.; Silveira, A., Jr. J. Org. Chem. 1978, 43, 358-360.
35. (a) Myers, A. G.; Alauddin, M. M.; Fuhry, M. A. M.; Dragovich, P. S.; Finney, N. S.; Harrington, P. M. Tetrahedron Lett. 1989, 30, 6997-7000.
36. (b) Hall, R. G.; Trippett, S. Tetrahedron Lett. 1982, 23, 2603-2604.
37. (a) Herndon, J. W.; Wang, H. J. Org. Chem. 1998, 63, 4562-4563.
38. (b) Arnold, Z.; Holy, A. Collect. Czech. Chem. Commun. 1961, 26, 3059-3073.
39. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470.
40. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
41. Comins, D. L.; Killpack, M. O. J. Org. Chem. 1987, 52, 104-109.
42. Mukai, C.; Hirose, T.; Teramoto, S.; Kitagaki, S. Tetrahedron 2005, 61, 10983-10994.
43. Plé, N.; Turck, A.; Heynderickx, A.; Quéguiner, G. Tetrahedron 1998, 54, 9701-9710.
44. In the study of intramolecular [4 + 2] cycloaddition on the basis of this methodology, improvement in the cycloadduct yield was observed when a reaction mixture was heated under reflux. See ref 4.