Mechanistic and exploratory investigations into the synthesis of 1,3,5-triaroylbenzenes from 1-aryl-2-propyn-1-ones and 1,3,5-triacetylbenzene from 4-methoxy-3-buten-2-one by cyclotrimerization in hot water in the absence of added acid or base

Journal of Organic Chemistry

Volumn 78, Issue 5, 2013, Pages 1949-1954

  Iwado, Tatsuya ^a   Hasegawa, Keiya ^a   Sato, Toshiyuki ^a   Okada, Masaki ^a   Sue, Kiwamu ^b   Iwamura, Hiizu ^a   Hiaki, Toshihiko ^a  

^a NIHON UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVES; KETONES; OLEFINS;

ACETOPHENONES; CONJUGATE ACID; CYCLOTRIMERIZATION; ISOLATED YIELD; NUCLEOPHILIC ATTACK; PURE WATER; REACTION MECHANISM; REACTION MIXTURE;

REACTION INTERMEDIATES;

ACETALDEHYDE; ACETOPHENONE DERIVATIVE; BENZENE DERIVATIVE; HOT WATER; SODIUM;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATE; CROSS REACTION; CYCLOTRIMERIZATION; DECOMPOSITION; FILTRATION; NUCLEOPHILICITY; PROTON TRANSPORT; SUBSTITUTION REACTION; SYNTHESIS; WATER TEMPERATURE;

EID: 84874610281     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301979p     Document Type: Article

References (47)

1. Pigge, F. C.; Ghasedi, F.; Rath, N. P. Tetrahedron Lett. 1999, 40, 8045-8048
2. Pigge, F. C.; Zheng, Z.; Rath, N. P. New J. Chem. 2000, 24, 183-185
3. Pigge, F. C.; Ghasedi, F. Tetrahedron Lett. 2000, 41, 6545-6549
4. Pigge, F. C.; Ghasedi, F.; Zheng, Z.; Rath, N. P.; Nichols, G.; Chickos, J. J. Chem. Soc., Perkin Trans. 2 2000, 2458-2464
5. Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1995, 117, 5550-5560
6. Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura, H. Chem.-Eur. J. 1996, 2, 259-264
7. Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura, H. Bull. Chem. Soc. Jpn. 1996, 69, 1483-1494
8. Vandendriessche, A.; Thomas, J.; Van Oosterwijck, C.; Huybrechts, J.; Dervaux, B.; D'hollander, S.; Du Prez, F.; Dehaen, W.; Smet, M. Eur. Polym. J. 2009, 45, 3196-3209
9. Jim, C. K. W.; Qin, A.; Lam, J. W. Y.; Liu, J.-Z.; Haeussler, M.; Tang, B. Z. Sci. China, Ser. B: Chem. 2008, 51, 705-708
10. Dong, H.; Qin, A.; Jim, C. K. W.; Lam, J.W. Y.; Haussler, M.; Tang, B. Z. J. Inorg. Organomet. Polym. 2008, 18, 201-205
11. Balasubramanian, K.; Selvaraj, P. S.; Venkataramani, P. S. Synthesis 1980, 29-30
12. Matsuda, K.; Nakamura, N.; Iwamura, H. Chem. Lett. 1994, 1765-1768
13. Iwamura, H.; Matsuda, K. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; VCH: Weinheim, 1995; pp 385-414.
14. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92
15. Reppe, W.; Schlichtig, O.; Klager, K.; Topel, T. Liebigs Ann. 1948, 560, 1-92
16. Reppe, W.; von Kutepow, N.; Magin, A. Angew. Chem. 1969, 81, 717-723
17. Angew. Chem., Int. Ed. Engl. 1969, 8, 727-733.
18. Meriwether, L. S.; Clothup, E. C.; Kennerly, G. W.; Reusch, R. N. J. Org. Chem. 1961, 26, 5155-5163
19. Reikhstel'd, V. O.; Makovetskii, K. L. Russ. Chem. Rev. 1966, 35, 510-523
20. Sigman, M. S.; Fatland, A. W.; Eaton, B. E. J. Am. Chem. Soc. 1998, 120, 5130-5131
21. Cadierno, V.; Garc a-Garrido, S. E.; Gimeno, J. J. Am. Chem. Soc. 2006, 128, 15094-15095
22. Jerome, K. S.; Parsons, E. J. Organometallics 1993, 12, 2991-2993
23. Borwieck, H.; Walter, O.; Dinjus, E.; Rebizant, J. J. Organomet. Chem. 1998, 570, 121-127
24. Tanaka, M.; Nakamura, K.; Iwado, T.; Sato, T.; Okada, M.; Sue, K.; Iwamura, H.; Hiaki, T. Chem.-Eur. J. 2011, 17, 606-612
25. Uematsu, M.; Franck, E. U. Ber. Bunsenges. Phys. Chem 1980, 95, 1586-1593
26. Uematsu, M.; Franck, E. U. J. Phys. Chem. Ref. Data 1980, 9, 1291-1306
27. Fernandez, D. P.; Goodwin, A. R. H.; Lemmon, E. W.; Sengers, J. M. H. L.; Williams, R. C. J. Phys. Chem. Ref. Data 1997, 1125-1166
28. Schneider, G. M. Ber. Bunsenges, Phys. Chem. 1972, 76, 325-331
29. Marshall, W. L.; Franck, E. U. J. Phys. Chem. Ref. Data 1981, 10, 295-304
30. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998; p 30.
31. Stadler, S.; Bräuchle, C.; Brandl, S.; Gompper, R. Chem. Mater. 1996, 8, 676-678
32. Diez-Barra, E.; Gonzalez, R; de la Hoz, A.; Rodriguez, A.; Sanchez Verdu, P. Tetrahedron Lett. 1997, 38, 8557-8560
33. L'abbé, G.; Haelterman, B.; Dehaen, W. J. Chem. Soc., Perkin Trans. 1 1994, 2203-2204
34. De Silva, A.; Lee, J.-K.; André, X.; Felix, N. M.; Cao, H. B.; Deng, H.; Ober, C. K. Chem. Mater. 2008, 20, 1606-1613
35. Karpuk, E.; Schollmeyer, D.; Meier, H. Eur. J. Org. Chem. 2007, 1983-1990
36. Riesgo, E. C.; Jin, X.; Thummel, R. P. J. Org. Chem. 1996, 61, 3017-3022
37. Gajardo, J.; Araya, J. C.; Moya, S. A.; Pardey, A. J.; Guerchais, V.; Le Bozec, H.; Aguirre, P. Appl. Organomet. Chem. 2006, 20, 272-276
38. Rahman, A. F. M. M.; Jahng, Y. Heteroat. Chem. 2007, 18, 650-656
39. Frank, R. L.; Varland, R. H. Org. Synth. 1947, 27, 91
40. Frank, R. L.; Varland, R. H. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, pp 829-830.
41. Alaimo, P. J.; Marshall, A.-L.; Andrews, D. M.; Langenhan, J. M. Org. Synth. 2010, 87, 192-200
42. Noy, R. S.; Gindin, V. A.; Erchov, B. A.; Kol'tsov, A. I.; Zubkov, V. A. Org. Magn. Reson. 1975, 7, 109-115
43. Martinson, P. Acta Chem. Scand. 1969, 23, 751-764
44. Rideout, D.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 7816-7817
45. Breslow, R. Acc. Chem. Res. 1991, 24, 159-164
46. J. Liu, J.; Cao, R.; Wang, Z.; Peng, W.; Song, H. Eur. J. Med. Chem. 2009, 44, 1737-1744
47. Talinli, N.; Karlinga, B. J. Heterocycl. Chem. 2004, 41, 205-209