Radical reactions in esters with alkoxy functionality chemistry an unusual alcohol moiety hydrogen abstraction

Tetrahedron Letters

Volumn 45, Issue 18, 2004, Pages 3685-3687

  Yan, Ming Chung ^a   Jang, Yeong Jiunn ^a   Wu, Jhenyi ^a   Lin, Yung Feng ^a   Yao, Ching Fa ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; HYDROGEN;

ADDITION REACTION; ALCOHOL OXIDATION; ARTICLE; ESTERIFICATION; GEOMETRY; HYDROGENATION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 1842736534     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.158     Document Type: Article

References (14)

1. Liu J.-T., Jang Y.-J., Shih Y.-K., Hu S.-R., Chu C.-M., Yao C.-F. J. Org. Chem. 66:2001;6021.
2. Jang Y.-J., Shih Y.-K., Liu J.-Y., Kuo W.-Y., Yao C.-F. Chem. Eur. J. 9:2003;2123.
3. Iwasaki M., Kobayashi Y., Li J.-P., Matsuzaka H., Ishii Y., Hidai M. J. Org. Chem. 56:1991;1922.
4. Eduardo P.-C., Norrby P.-O., Sjögren M., Vitagliano A., Felice V.D., Oslob J., Ishii S., O'Neill D., Åkermark B., Helquist P. J. Am. Chem. Soc. 118:1996;4299.
5. Petrov A.D., Nikishin G.I., Ogibin Y.N. Dokl. Akad. Nauk. 131:1960;580.
6. Nikishin G.I., Ogibin Y.N., Petrov A.D. Dokl. Akad. Nauk. 136:1961;1326.
7. Allen J.C., Cadogan J.I.G., Harris B.W., Hey D.H. J. Chem. Soc. 1962;4468.
8. Cazaux M., Lalande R. Bull. Soc. Chim. Fr. 2:1971;461.
9. Bennett J.E., Gilbert B.C., Lawrence S., Whitwood A.C., Holmes A.J. J. Chem. Soc., Perkin Trans. 2. 9:1996;1789.
10. Boland G.M., Donnelly G.M.X. Nat. Prod. Rep. 15:1998;241. and previous reviews in this series.
11. Engler T.A., LaTessa K.O., Iyengar R., Chai W., Agrios K. Bioorg. Med. Chem. 4:1996;1755.
12. Nakagawa M., Nakanishi K., Darko L.L., Vick J.A. Tetrahedron Lett. 23:1982;3855.
13. Gulacsi K., Litkei G., Antus S., Szantay C., Darko L.L., Szelenyi J., Hasko G., Vizi S.E. Arch. Pharm. Pharm. Med. Chem. 334:2001;53.
14. General procedure for the reaction of esters with β-nitrostyrene - preparation of (E)-3af, (E)-1-methyl-3-phenyl-allyl acetate: β-Nitrostyrene 1a (149.2 mg, 1.0 mmol) and benzoyl peroxide (605.6 mg, 2.5 mmol) were placed in ethyl acetate 2f (10 mL). The mixture was stirred for 5 h under refluxing condition and then concentrated in vacuo. After the solvent evaporated, the residue was purified by column chromatography on silica gel and yielded the desired product (E)-3af in 50% yield.