Reactions of azulene and guaiazulene with all-trans-retinal and trans-cinnamaldehyde: comparative studies on spectroscopic, chemical, and electrochemical properties of monocarbenium-ions stabilized by expanded π-electron systems with an azulenyl or 3-guaiazulenyl group

Tetrahedron

Volumn 63, Issue 18, 2007, Pages 3882-3893

  Takekuma, Shin ichi ^a   Mizutani, Kazutaka ^a   Inoue, Kanako ^a   Nakamura, Masaru ^a   Sasaki, Masato ^a   Minematsu, Toshie ^a   Sugimoto, Kunihisa ^b   Takekuma, Hideko ^a  

^a KINKI UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

All trans retinal; Azulene; Carbenium ions; Electrochemical behavior; Guaiazulene; NaBH4 reduction; Spectroscopic properties; trans Cinnamaldehyde; X ray crystal structure

Indexed keywords

1 (3 GUAIAZULENYL) 2 PROPEN 1 YLIUM; 1 (3 GUAIAZULENYL) 3 PHENYL 2 PROPEN 1 YLIUM HEXAFLUOROPHOSPHATE; 1 AZULENYL 2 PROPEN 1 YLIUM; 1 AZULENYL 3 PHENYL 2 PROPEN 1 YLIUM; 1 AZULENYL 3,7 DIMETHYL 9 (2,6,6 TRIMETHYL 1 CYCLOHEXEN 1 YL) 2,4,6,8 NONATETRAEN 1 YLIUM HEXAFLUOROPHOSPHATE; AZULENE; CARBENOID; CINNAMALDEHYDE; ETHER; FLUORINE DERIVATIVE; GUAIAZULENE; PHENYL GROUP; PHOSPHORIC ACID DERIVATIVE; PROPYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPARATIVE STUDY; CRYSTAL STRUCTURE; ELECTROCHEMICAL ANALYSIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 33947639067     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.071     Document Type: Article

References (48)

1. Oda M., Uchiyama T., Kajioka T., Hashimoto T., Miyatake R., and Kuroda S. Heterocycles 53 (2000) 2071-2077
2. Oda M., Fukuta A., Kajioka T., Uchiyama T., Kainuma H., Miyatake R., and Kuroda S. Tetrahedron 56 (2000) 9917-9925
3. Oda M., Fukuta A., Uchiyama T., Kajioka T., and Kuroda S. Recent Res. Dev. Org. Chem. 6 (2002) 543-563
4. Okazaki T., and Laali K.K. Org. Biomol. Chem. 1 (2003) 3078-3093
5. Reid D.H., Stafford W.H., Stafford W.L., McLennan G., and Voigt A. J. Chem. Soc. (1958) 1110-1117
6. Kirby E.C., and Reid D.H. J. Chem. Soc. (1960) 494-501
7. Fraser M., and Raid D.H. J. Chem. Soc. (1963) 1421-1429
8. Hünig S., Scheutzow D., and Friedrich H.J. Angew. Chem. 76 (1964) 818
9. Hünig S., and Ort B. Liebigs Ann. Chem. (1984) 1905-1935
10. Hünig S., and Ort B. Liebigs Ann. Chem. (1984) 1936-1951
11. Hünig S., and Ort B. Liebigs Ann. Chem. (1984) 1959-1971
12. Ito S., Fujita M., Morita N., and Asao T. Bull. Chem. Soc. Jpn. 73 (2000) 721-727
13. Ito S., Morita N., and Asao T. Bull. Chem. Soc. Jpn. 73 (2000) 1865-1874
14. Ito S., Kikuchi S., Okujima T., Morita N., and Asao T. J. Org. Chem. 66 (2001) 2470-2479
15. Ito S., Kubo T., Morita N., Ikoma T., Tero-Kubota S., and Tajiri A. J. Org. Chem. 68 (2003) 9753-9762
16. Ito S., Kubo T., Kondo M., Kabuto C., Morita N., Asao T., Fujimori K., Watanabe M., Harada N., and Yasunami M. Org. Biomol. Chem. 1 (2003) 2572-2580
17. Ito S., Kawakami J., Tajiri A., Ryuzaki D., Morita N., Asao T., Watanabe M., and Harada N. Bull. Chem. Soc. Jpn. 78 (2005) 2051-2065
18. Naya S., and Nitta M. J. Chem. Soc., Perkin Trans. 2 (2001) 275-281
19. Cristian L., Sasaki I., Lacroix P.G., Donnadieu B., Asselberghs I., Clays K., and Razus A.C. Chem. Mater. 16 (2004) 3543-3551
20. Muthyala R.S., Alam M., and Liu R.S.H. Tetrahedron Lett. 39 (1998) 5-8
21. Asato A.E., Li X.-Y., Mead D., Patterson G.M.L., and Liu R.S.H. J. Am. Chem. Soc. 112 (1990) 7398-7399
22. Muthyala R., Watanabe D., Asato A.E., and Liu R.S.H. Photochem. Photobiol. 74 (2001) 837-845
23. Takekuma S., Sasaki M., Takekuma H., and Yamamoto H. Chem. Lett. (1999) 999-1000
24. Takekuma S., Takata S., Sasaki M., and Takekuma H. Tetrahedron Lett. 42 (2001) 5921-5924
25. Takekuma S., Tanizawa M., Sasaki M., Matsumoto T., and Takekuma H. Tetrahedron Lett. 43 (2002) 2073-2078
26. Sasaki M., Nakamura M., Hannita G., Takekuma H., Minematsu T., Yoshihara M., and Takekuma S. Tetrahedron Lett. 44 (2003) 275-279
27. Sasaki M., Nakamura M., Uriu T., Takekuma H., Minematsu T., Yoshihara M., and Takekuma S. Tetrahedron 59 (2003) 505-516
28. Nakamura M., Sasaki M., Takekuma H., Minematsu T., and Takekuma S. Bull. Chem. Soc. Jpn. 76 (2003) 2051-2052
29. Takekuma S., Sasaki K., Nakatsuji M., Sasaki M., Minematsu T., and Takekuma H. Bull. Chem. Soc. Jpn. 77 (2004) 379-380
30. Nakatsuji M., Hata Y., Fujihara T., Yamamoto K., Sasaki M., Takekuma H., Yoshihara M., Minematsu T., and Takekuma S. Tetrahedron 60 (2004) 5983-6000
31. Takekuma S., Hata Y., Nishimoto T., Nomura E., Sasaki M., Minematsu T., and Takekuma H. Tetrahedron 61 (2005) 6892-6907
32. Takekuma S., Takahashi K., Sakaguchi A., Shibata Y., Sasaki M., Minematsu T., and Takekuma H. Tetrahedron 61 (2005) 10349-10362
33. Takekuma S., Takahashi K., Sakaguchi A., Sasaki M., Minematsu T., and Takekuma H. Tetrahedron 62 (2006) 1520-1526
34. Takekuma S., Hirosawa M., Morishita S., Sasaki M., Minematsu T., and Takekuma H. Tetrahedron 62 (2006) 3732-3738
35. Takekuma S., Sonoda K., Fukuhara C., and Minematsu T. Tetrahedron 63 (2007) 2472-2481
36. Takekuma S., Tone K., Sasaki M., Minematsu T., and Takekuma H. Tetrahedron 63 (2007) 2490-2502
37. Matsubara Y., Yamamoto H., and Nozoe T. In: Atta-ur-Rahman (Ed). Stereoselective Synthesis (Part I). Studies in Natural Products Chemistry Vol. 14 (1994), Elsevier, Amsterdam 313-354
38. Katagiri K., Oguchi Y., and Takasu Y. Nippon Kagaku Kaishi (1986) 387-392
39. The reaction of 1 with all-trans-retinal in methanol (or diethyl ether) in the presence of hexafluorophosphoric acid at -10 °C for 1 h in a dark room gave the same result.
40. 3CN) nm (log ε): 235 (4.23), 270sh (4.70), 273 (4.71), 278 (4.66), 293sh (3.54), 324 (3.49), 338 (3.63), 350 (2.82), 576 (2.53), 622sh (2.45), and 683sh (2.02).
41. -10).
42. 2O) displayed a small mass loss between 125 and 130 °C of 0.5% that corresponded to surface dehydration and loss of the extra-framework water molecule (calculated 0.5%).
43. 3CN) nm (log ε): 213 (4.10), 244 (4.39), 284 (4.61), 301sh (4.03), 348 (3.65), 365 (3.46), 600 (2.68), 648sh (2.61), and 721sh (2.20).
44. Details based on ab initio calculations for 3-6 are further currently under intensive investigation.
45. Zeller K.-P. Methoden der Organishen Chemie. 4th ed. Vol. V/2c (1985), Georg Thieme, Stuttgart p 127
46. Bouwstra J.A., Schouten A., and Kroon J. Acta Crystallogr. C40 (1984) 428-431
47. Santarsiero B.D., James M.N.G., Mahendran M., and Childs R.F. J. Am. Chem. Soc. 112 (1990) 9416-9418
48. -10).