Uncatalyzed Meerwein-Ponndorf-Oppenauer-Verley Reduction of Aldehydes and Ketones under Supercritical Conditions

Journal of Organic Chemistry

Volumn 69, Issue 5, 2004, Pages 1492-1496

  Sominsky, Lena ^a   Rozental, Esther ^a   Gottlieb, Hugo ^a   Gedanken, Aharon ^a   Hoz, Shmaryahu ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ENTROPY; KETONES; REACTION KINETICS; REDUCTION;

REDUCING AGENTS; TRANSITION STATES;

ALDEHYDES;

ACETOPHENONE; ALCOHOL; ALDEHYDE; BENZALDEHYDE; CARBONYL DERIVATIVE; KETONE;

AB INITIO CALCULATION; ARTICLE; CALCULATION; CATALYSIS; CHEMICAL REACTION; HEAT TREATMENT; REDUCTION; THERMODYNAMICS;

EID: 1442349014     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035251f     Document Type: Article

References (15)

1. Meerwein, H.; Schmidt, R. Justus Liebigs Ann. Chem. 1925, 39, 221.
2. Pondorf, W. Angew. Chem. 1926, 39, 138.
3. Verley, M. Bull. Soc. Chim. Fr. 1925, 37, 871.
4. Oppenauer, R. V. Recl. Trav. Chim. 1937, 56, 137.
5. Fujita, M.; Takarada, Y.; Sugimura, T.; Tai, A. Chem. Commun. 1997, 17, 1631-1632.
6. Akamanchi, K. G.; Chaudhari, B. A. Tetrahedron Lett. 1977, 38, 6925-6928.
7. Campbell, E. J.; Zhou, H.; Nguyen, S. T. Org. Lett. 2001, 3, 2391-2393.
8. Ooi, T.; Otsuka, H.; Miura, T.; Ichikawa, H.; Maruoka, K. Org. Lett. 2002, 4, 2669-2672,
9. Ishihara, T.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 5664-5665.
10. Aramendia, M. A.; Borau, V.; Jimenez, C.; Marinas, J. M.; Romero, F. J. Catal. Lett. 1999, 58, 53-58.
11. Ajjou, A. N. Tetrahedron Lett. 2001, 42, 13-15.
12. Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. J. Org. Chem. 2003, 68, 1601-1602.
13. Schrekker, H, S.; de Bolster, M. W. G.; Orru, R. V. A.; Wessjohann, L. A. J. Org. Chem. 2002, 67, 1975.
14. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.4; Gaussian, Inc.: Pittsburgh, PA, 1998.
15. An isodesmic equation is one in which there are equal numbers of each type of bond on each side. Clark, T. A Handbook of Computational Chemistry; Wiley: New York, 1985; p 97.