Lithium azidohydridodiisobutylaluminate in THF as an efficient azide donor

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4337-4338

  Youn, Yong Sik ^a   Cho, In Sik ^a   Chung, Bong Young ^a  

^a Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; EPOXIDE; LITHIUM DERIVATIVE;

ARTICLE; CHEMICAL BINDING; DRUG SYNTHESIS; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0032508076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00766-7     Document Type: Article

References (10)

1. 1. (a) Chaloner, P. A. Preparation and Use of Organoaluminum Compounds in Organic Synthesis. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Eds.;John Wiley: New York, 1987; vol. 4. pp. 412-472.
2. (b) Eisch, J. J. Hydroalumination of C=C and C=C. In Comprehensive Organic Synthesis; Trost, B. M.; Freming, I., Eds.; Pergamon Press: Oxford, 1991; vol. 8. pp. 733-761.
3. (c) Paquette, L. A. Encyclopedia of Reagents for Organic Synthesis; John Wiley: New York, 1995; pp. 1908-1912.
4. (d) Kim, S; Ahn, K. H. J. Org. Chem. 1984, 49, 1717-1724.
5. 2. Lee, H. W.; Kim, Y. J.; Chung, B. Y. Bull. Korean Chem. Soc. 1997, 18, 1144-1145.
6. 3. Lithium azide or sodium azide did not form the ate complex with DIBAH in dichloromethane. Reaction of benzoyl chloride with the excess amounts of the resulting suspension produced benzyl alcohol only.
7. 4. Sodium azide, potassium azide, or cesium azide with DIBAH in THF, and potassium azide or cesium azide with DIBAH in dichloromethane also reacted with benzoyl chloride to afford benzoyl azide.
8. 5. Other acid chlorides such as phenacetyl chloride, cinnamoyl chloride, and p-chlorobenzoyl chloride also gave the corresponding acid azide in 93, 90, and 90 % yield, respectively.
9. 6. (a) Previous references are cited in ref, 2.
10. (b) Saito, A.; Saito, K.; Tanaka, A.; Oritani, T. Tetrahedron Lett. 1997, 38, 3955-3958.