Scandium trifluoromethanesulphonate as an active catalyst in the decarbonylation of aromatic aldehydes

Tetrahedron

Volumn 52, Issue 33, 1996, Pages 11045-11052

  Castellani, Carla Bisi ^a   Carugo, Oliviero ^a   Giusti, Manuel ^a   Leopizzi, Claudia ^a   Perotti, Angelo ^a   Invernizzi, Anna Gamba ^a   Vidari, Giovanni ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AROMATIC COMPOUND;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030581392     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00622-9     Document Type: Article

References (35)

1. 1. For application of rare earth elements in organic synthesis see following reviews and references cited therein. (a) Molander, G. A. Chem. Rev. 1992, 92, 29.
2. (b) Kagan, H. B.; Nancy, J. L. Tetrahedron 1986, 42, 6573.
3. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press; London, 1994.
4. (d) Kobayashi, S. Synlett 1994, 689.
5. 2. For our previous contributions in this field see: (a) Bisi Castellani, C.; Carugo, O.; Tomba, C.; Invernizzi Gamba, A. Inorg. Chem. 1988, 27, 3965.
6. (b) Carugo, O.; Bisi Castellani, C.; Ghigna, P.; Rizzi, M. Eur. J. Solid State Inorg. Chem. 1990, 28, 425.
7. (c) Bisi Castellani, C.; Carugo, O.; Perotti, A.; Sacchi, D.; Invernizzi Gamba, A.; Vidari, G. J. Mol. Cat. 1993, 85, 65.
8. (d) Garlaschelli, L.; Vidari, G. Tetrahedron Lett. 1990, 31, 5815.
9. 3. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc. Chem. Comm. 1995, 1527.
10. 4. (a) Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545.
11. (b) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett. 1995, 1153.
12. 5. (a) Schubert, W. H.; Latourette, H. K. J. Am. Chem. Soc. 1952, 74, 1829.
13. th Ed.; Wiley, New York, 1992.
14. 6. Taylor, R. Electrophilic Aromatic Substitution; Wiley; New York, 1990.
15. 3 as a catalyst in organic synthesis see: (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
16. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis, 1995, 1195.
17. (c) Fuzukawa, S.-i.; Tsuchimoto, T.; Hotaka, T. Synlett. 1995, 1077.
18. (d) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413 and references cited therein.
19. 8. Burkett, H.; Schubert, W. M.; Schultz, F.; Murphy, R. B.; Talbott, R. J. Am. Chem. Soc. 1959, 81, 3923.
20. 3 we observed the formation of condensation by-products which will be reported in a forthcoming paper.
21. 10. The concomitant decomposition of 1 was very slow at the concentration (ca. 10-5 M) suitable for the spectrophotometric studies and did not affect measurements significantly.
22. 13C): -2.60 for C-1, +4.43 for C-2, +0.79 for C-3, +7.82 for C-4, +3.93 for C-5, +1.25 for C-6, +1.07 for C-7.
23. 12. Job, P. Ann. Chim. 1928, 9, 133.
24. 13. (a) Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
25. (b) Scott, R. L. Rec. Trav. Chim. 1956, 75, 787.
26. 2O caused the UV spectrum of 2 to become that of uncomplexed aldehyde 1.
27. 2O ( Di Bernardo, P.; Cioppin, G.R.; Portanova, R.; Zanonato, P.L. Inorg.Chim.Acta 1993, 207, 85).
28. 3 in MeCN solution.
29. 3+ can reach 9 ( Bisi Castellani, C.; Carugo, O.; Giusti, M.; Sardone, N. Eur. J .Solid State Inorg.Chem. 1995,32, 1089).
30. 3+ but also by the lack of coplanarity with the aromatic ring due to steric hindrance with the o-methoxyl groups.
31. 19. The catalytic activity of lanthanide (III) ions in acetal formation is well documented; see: (a) Luche, J.L.; Gemal, A.L. J.Chem.Soc.Chem.Commun. 1978, 976.
32. (b) reference 2a.
33. 3.
34. 8.
35. 1La band in the UV spectra of 1 in MeCN solution.