1,3-Dipolar cycloaddition of nitrile oxides to methyl 3-(p- nitrobenzoyloxy)acrylate: Methyl 3-(p-nitrobenzoyloxy)acrylate as a methyl propiolate equivalent with reverse regioselectivity

Journal of Heterocyclic Chemistry

Volumn 37, Issue 1, 2000, Pages 75-78

  Zong, Kyukwan ^a   Shin, Seung Il ^a   Jeon, Dong Ju ^a   Lee, Jung No ^a   Ryu, Eung K ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; BENZONITRILE; ISOXAZOLE DERIVATIVE; NITRILE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034110031     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570370112     Document Type: Article

References (7)

1. R. Huisgen, 1,3-Dipolar Cycloaddition Chemistry, Vol 1, A. Padwa, ed, Wiley-Intersciense, Inc., New York, 1984, pp 1-176; D. P. Curran, Advances in Cycloadditions, Vol. 1, D. P. Curran, ed, JAI Press, Inc., Greenwich, CT, 1988, pp 280-520.
2. R. Huisgen, 1,3-Dipolar Cycloaddition Chemistry, Vol 1, A. Padwa, ed, Wiley-Intersciense, Inc., New York, 1984, pp 1-176; D. P. Curran, Advances in Cycloadditions, Vol. 1, D. P. Curran, ed, JAI Press, Inc., Greenwich, CT, 1988, pp 280-520.
3. The regioselectivity could be predominantly reversed by using 3-(dimethylamino)acrylic esters and 3-pyrrolidinoacrylic esters, see: M. Christl, R. Huisgen, and R. Sustmann, Chem. Ber., 106, 3275 (1973); G. Stork and J. E. Mcmurry, J. Am. Chem. Soc., 89, 5461 (1967).
4. The regioselectivity could be predominantly reversed by using 3-(dimethylamino)acrylic esters and 3-pyrrolidinoacrylic esters, see: M. Christl, R. Huisgen, and R. Sustmann, Chem. Ber., 106, 3275 (1973); G. Stork and J. E. Mcmurry, J. Am. Chem. Soc., 89, 5461 (1967).
5. E. Coutouli-Argyropoulou and E. Thessalonikes, J. Heterocyclic Chem., 28, 429 (1991).
6. E. Lee, C. M. Park, and J. S. Yun, J. Am. Chem. Soc., 117, 8017 (1995).
7. P. A. Wade, N. V. Amin, H-K. Yen, D. T. Price, and G. F. Huhn, J. Org. Chem., 49, 4595 (1984).