Conversions of unsymmetrical benzoins in basic media

Arkivoc

Volumn 2005, Issue 8, 2004, Pages 4-9

  Ivonin, Sergey P ^a   Lapandin, Andrey V ^a  

^a OLES HONCHAR DNIPRO NATIONAL UNIVERSITY   (Ukraine)

Author keywords

Basic catalysis; Benzoins; Indoles; Isomerization; Reaction mechanisms

Indexed keywords

BASE; BENZOIN; INDOLE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL REACTION; ISOMERIZATION; TEMPERATURE;

EID: 15444377962     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
2. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
3. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
4. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
5. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
6. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
7. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
8. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
9. For some examples of recent research in this area, see: (a) Shi, Y.; Corrie, J. E. T.; Wan, P. J. Org. Chem. 1997, 62, 8278. (b) Pei, W.; Li, S.; Nie, X.; Li, Y.; Pei, J.; Chen, B.; Wu, J.; Ye, X. Synthesis 1998, 1298. (c) Šimon, P.; Landl, M.; Breza, M. Dyes & Pigments 1999, 43, 227. (d) Pandey, V. K.; Shukla, A. Indian J. Chem., Sect. B 1999, 38, 1381. (e) Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159. (f) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589. (g) Mohan, J. A. Indian J. Chem., Sect. B 2001, 40, 368. (h) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124. (i) D'Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877.
10. For some examples of recent research in this area, see: (a) White, M. J.; Leeper, F. J. J. Org. Chem. 2001, 66, 5124. (b) Aoyagi, Y.; Iijima, A.; Williams, R. M. J. Org. Chem. 2001, 66, 8010. (c) Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5288.
11. For some examples of recent research in this area, see: (a) White, M. J.; Leeper, F. J. J. Org. Chem. 2001, 66, 5124. (b) Aoyagi, Y.; Iijima, A.; Williams, R. M. J. Org. Chem. 2001, 66, 8010. (c) Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5288.
12. For some examples of recent research in this area, see: (a) White, M. J.; Leeper, F. J. J. Org. Chem. 2001, 66, 5124. (b) Aoyagi, Y.; Iijima, A.; Williams, R. M. J. Org. Chem. 2001, 66, 8010. (c) Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5288.
13. (a) Roger, R.; Reid, K. C.; Wood, R. J. Chem. Soc. 1954, 3453.
14. (b) Forisher, J.; Montavon, F.; Pfoertner, K.-H.; Schönholzer, P. Helv. Chim. Acta 1985, 68, 592.
15. (a) Jenkins, S. S. J. Am. Chem. Soc. 1931, 53, 3115.
16. (b) Luis, E. M. J. Chem. Soc. 1932, 2547.
17. Julian, P. L.; Passler, W. J. Am. Chem. Soc. 1932, 54, 4756.
18. Weinstock, H. H.; Fuson, R. C. J. Am. Chem. Soc. 1936, 58, 1986.
19. (e) Ide, W. S.; Buck, J. S. In Organic Reactions. Adams, R. Ed. Wiley, New York, 1948; Vol. 4, pp. 269-304.
20. Ivonin, S. P.; Lapandin, A. V.; Anishchenko, A. A.; Shtamburg, V. G. Synth. Commun. 2004, 34, 451.
21. (a) Ivonin, S. P.; Lapandin, A. V.; Shtamburg, V. G. Chem. Heterocycl. Comp. 2004, 40, 154.
22. (b) Ivonin, S. P.; Lapandin, A. V. Synth. Commun. 2004, 34 (20), in press.
23. Pawelka, Z.; Kryachko, E. S.; Zeegers-Huyskens, T. Chem. Phys. 2003, 287, 143.
24. Yoshima, S.; Yamamoto, K. Yakugaku Zasshi 1972, 92, 359; Chem. Abstr. 1972, 77, 5264p
25. Yoshima, S.; Yamamoto, K. Yakugaku Zasshi 1972, 92, 359; Chem. Abstr. 1972, 77, 5264p