Isomerization of 2-(2-propenoxy)phenyllithium: Tandem anionic cyclization-γ-elimination

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5435-5436

  Bailey, William F ^b   Punzalan, Eric R ^a,b  

^a DE LA SALLE UNIVERSITY   (Philippines)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM DERIVATIVE; PHENOL DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 15844416299     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01142-2     Document Type: Article

References (10)

1. 1. Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, Mechanisms of Importance in Synthesis; pp 251-273.
2. 2. To date, the only published investigations of heteroatom-containing 5-hexenyllithiums involve 2-oxa-, 3-oxa-, and 4-oxa-5-hexenyllithiums, see: (a) Broka, C. A.; Lee, W. J.; Shen, T. J. Org. Chem. 1988, 53, 1336.
3. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981.
4. (c) Bailey, W. F.; Zarcone, L. M. J. Tetrahedron Lett. 1991, 32, 4425.
5. (d) Bailey, W. F.; Punzalan, E. R.; Zarcone, L. M. J. Heteroat. Chem. 1992, 3, 55.
6. 3. (a) Bailey, W. F.; Jiang, X.-L. J. Org. Chem. 1996, 61, 2596.
7. (b) Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, 2594.
8. 4. 2-Iodo-1-(2-propenoxy)benzene was prepared by allylation of 2-iodophenol as previously described: Beckwith, A. L. J.; Gara, W. B. J. Chem. Soc., Perkin Trans. 2 1975, 795.
9. 5. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
10. 6. Kitamura, T.; Imagawa, T.; Kawanisi, M. Tetrahedron 1978, 34, 3451.