Montmorillonite clay-catalyzed cyclotrimerization and oxidation of aliphatic aldehydes

Tetrahedron Letters

Volumn 51, Issue 5, 2010, Pages 826-827

  Dintzner, Matthew R ^a   Mondjinou, Yawo A ^a   Pileggi, Dominic J ^a  

^a DEPAUL UNIVERSITY   (United States)

Author keywords

1,3,5 Trioxanes; Aliphatic aldehydes; Carboxylic acids; Cyclotrimerization; Green chemistry; Montmorillonite clay; Oxidation

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID; MONTMORILLONITE;

ARTICLE; CATALYSIS; CLAY; OXIDATION; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE;

EID: 73049094813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.009     Document Type: Article

References (26)

1. Dintzner M.R., Mondjinou Y.A., and Unger B. Tetrahedron Lett. 50 (2009) 6639
2. Dintzner M.R., Little A.J., Pacilli M., Pileggi D.J., Osner Z.R., and Lyons T.W. Tetrahedron Lett. 48 (2007) 1577
3. Dintzner M.R., Wucka P.R., and Lyons T.W. J. Chem. Educ. 83 (2006) 270
4. Dintzner M.R., Lyons T.W., Akroush M.H., Wucka P., and Rzepka A.T. Synlett 5 (2005) 785
5. Dintzner M.R., McClelland K.M., Morse K.M., and Akroush M.H. Synlett 11 (2004) 2028
6. Dintzner M.R., Morse K.M., McClelland K.M., and Coligado D.M. Tetrahedron Lett. 45 (2004) 79
7. Withycombe, D. A.; Mookherjee, B. D.; Vock, M. H.; Vinals, J. F. US 4,093,752, June 6, 1978.
8. Segawa T., Hosokawa H., Yokoro K., Uchino H., and Okada K. Oyo Yakuri 14 (1977) 391-396
9. Ishikawa, M.; Kagawa, N.; Hagiwara, M.; Koboshi, S. Jpn Kokai Tokkyo Koho JP 04,024,634, January 28, 1992.
10. Ueno, Y.; Saeki, Y.; Akiyama, T.; Fujita, M. US 4,123,525, October 31, 1978.
11. Hon Y., and Lee C. Tetrahedron 57 (2001) 6181-6188
12. Dermer O.C., and Jenkins A.M. J. Org. Chem. 24 (1959) 869
13. Kagan J., Agdeppa D.A., Chang A.I., Chen S., Harmata M.A., Melnick B., Patel G., Poorker C., and Singh S.P. J. Org. Chem. 46 (1981) 2916
14. Wakasugi T., Tonouchi N., Miyakawa T., Ishizuka M., Yamauchi T., Itsuno S., and Ito K. Chem. Lett. (1992) 171
15. Nishiyama K., and Oba M. Bull. Chem. Soc. Jpn. 60 (1987) 2289
16. Chandrasekhar S., Takhi M., Ravindra Reddy Y.R., Mohapatra S., Rama Rao C.R., and Venkatram Reddy K.V. Tetrahedron 53 (1997) 14997
17. Peidro L., Le Roux C., Laporterie A., and Dubac J. J. Organomet. Chem. 521 (1996) 397
18. Denmark S.E., and Almstead N.G. Tetrahedron 48 (1992) 5565
19. Sato S., Furuta H., Sodesawa T., and Nozaki F. J. Chem. Soc., Perkin Trans. 2 (1993) 385
20. Mori H., Yamazaki T., Ozawa S., and Ogino Y. Bull. Chem. Soc. Jpn. 66 (1993) 2498
21. Astle M.J., and Pinns M.L. J. Org. Chem. 24 (1959) 56
22. Camarena R., Cano A.C., Delgado F., Zuniga N., Alvarez C., and Garcia O. Tetrahedron Lett. 34 (1993) 6857
23. Denmark et al, observed similar results with metal-based Lewis acids. Denmark S.E., Wilson T., Wilson T.M. J. Am. Chem. Soc. 110 (1988) 984
24. Blanc P.Y., Perret A., and Teppa F. Helv. Chim. Acta 47 (1964) 567
25. Larock R.C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations (1989), VCH, New York and references cited therein
26. 3) δ 182.3, 43.0, 28.8, 25.7, 25.45.