Preparation of 1,2- and 1,4-diols via selective cleavage of C- benzotriazole bonds in reductive lithiations of N-(α-alkoxy-benzyl- and - allyl-)benzotriazoles

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6437-6440

  Katritzky, Alan R ^a   Bao, Weiliang ^a   Qi, Ming ^a   Fali, Clara N ^a   Prakash, Indra ^b  

^a University of Florida   (United States)

^b Monsato Nutr and Consumer Sector   (United States)

Author keywords

Carbanions; Diols; Lithium compounds

Indexed keywords

ALCOHOL DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; CARBONYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; REACTION ANALYSIS;

EID: 0032171678     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01390-2     Document Type: Article

References (14)

1. 1. (a) Najera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
2. (b) Vus, M. Chem. Soc. Rev. 1996, 25, 155-161.
3. 2. Maercker, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 972-989.
4. 3. (a) Almena, J.; Foubelo, F., Yus, M. J. Org. Chem. 1994, 59, 3210-3215.
5. (b) Almena, J.; Foubelo, F., Yus, M. Tetrahedron 1994, 50, 5775-5782.
6. 4. Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev., 1998, 98, 409-548.
7. 5. (a) Katritzky, A. R.; Qi, M. J. Org. Chem. 1997, 62, 4116-4120.
8. (b) Katritzky, A. R.; Fall, C. N.; Qi, M. Tetrahedron Lett. 1998, 39, 363-366.
9. 6. Katritzky, A. R.; Fali, C. N.; Qi, M. Tetrahedron Lett. 1998, 39, 2289-2292.
10. 7. Katritzky, A. R.; Qi, M.; Feng, D.; Nichols, D. A. J. Org. Chem. 1997, 62, 4121-4124.
11. 8. (a) Katritzky, A. R.; Lang, H.; Wang, Z.; Zhang, Z.; Song, H. J. Org. Chem. 1995, 60, 7619-7624.
12. (b) Katritzky, A. R.; Zhang, G.; Jiang, J. J. Org. Chem. 1995, 60, 7589-7596.
13. 13C NMR spectra, and novel products gave satisfactory microanalyses or HRMS.
14. - has been recently surveyed, see Guijarro, A.; Yus, M. Tetrahedron Lett. 1996, 37, 5593-5596.