Nucleophilic Substitution of Methyl β-Chloro-(3-bromo-2,4,6-trimethyl)cinnamate

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5634-5637

  Yannai, Michal Beit ^a   Rappoport, Zvi ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042989345     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970157i     Document Type: Article

References (22)

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2. (b) Modena, G. Acc Chem. Res. 1971, 4, 73.
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4. (d) Shainyan, B. Russ. Chem. Rev. 1986, 55, 511.
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6. (a) Bunnett, J. F.; Garbisch, E. W., Jr.; Pruitt, H. M. J. Am. Chem. Soc. 1957, 79, 385. For element effect in vinylic systems, see ref 1 and: (b) Rappoport, Z.; Topol, A. J. Chem. Soc., Perkin Trans. 2 1975, 863. (c) Rappoport, Z.; Rav-Acha, C. Tetrahedron Lett. 1984, 25, 117. (d) Avramovitch, B.; Weyerstahl, P.; Rappoport, Z. J. Am. Chem. Soc. 1987, 109, 6687. (e) Hoz, S.; Basch, H.; Wolk, J. L.; Rappoport, Z.; Goldberg, M. J. Org. Chem. 1991, 56, 5424.
7. (a) Bunnett, J. F.; Garbisch, E. W., Jr.; Pruitt, H. M. J. Am. Chem. Soc. 1957, 79, 385. For element effect in vinylic systems, see ref 1 and: (b) Rappoport, Z.; Topol, A. J. Chem. Soc., Perkin Trans. 2 1975, 863. (c) Rappoport, Z.; Rav-Acha, C. Tetrahedron Lett. 1984, 25, 117. (d) Avramovitch, B.; Weyerstahl, P.; Rappoport, Z. J. Am. Chem. Soc. 1987, 109, 6687. (e) Hoz, S.; Basch, H.; Wolk, J. L.; Rappoport, Z.; Goldberg, M. J. Org. Chem. 1991, 56, 5424.
8. (a) Bunnett, J. F.; Garbisch, E. W., Jr.; Pruitt, H. M. J. Am. Chem. Soc. 1957, 79, 385. For element effect in vinylic systems, see ref 1 and: (b) Rappoport, Z.; Topol, A. J. Chem. Soc., Perkin Trans. 2 1975, 863. (c) Rappoport, Z.; Rav-Acha, C. Tetrahedron Lett. 1984, 25, 117. (d) Avramovitch, B.; Weyerstahl, P.; Rappoport, Z. J. Am. Chem. Soc. 1987, 109, 6687. (e) Hoz, S.; Basch, H.; Wolk, J. L.; Rappoport, Z.; Goldberg, M. J. Org. Chem. 1991, 56, 5424.
9. (a) Bunnett, J. F.; Garbisch, E. W., Jr.; Pruitt, H. M. J. Am. Chem. Soc. 1957, 79, 385. For element effect in vinylic systems, see ref 1 and: (b) Rappoport, Z.; Topol, A. J. Chem. Soc., Perkin Trans. 2 1975, 863. (c) Rappoport, Z.; Rav-Acha, C. Tetrahedron Lett. 1984, 25, 117. (d) Avramovitch, B.; Weyerstahl, P.; Rappoport, Z. J. Am. Chem. Soc. 1987, 109, 6687. (e) Hoz, S.; Basch, H.; Wolk, J. L.; Rappoport, Z.; Goldberg, M. J. Org. Chem. 1991, 56, 5424.
10. (a) Bunnett, J. F.; Garbisch, E. W., Jr.; Pruitt, H. M. J. Am. Chem. Soc. 1957, 79, 385. For element effect in vinylic systems, see ref 1 and: (b) Rappoport, Z.; Topol, A. J. Chem. Soc., Perkin Trans. 2 1975, 863. (c) Rappoport, Z.; Rav-Acha, C. Tetrahedron Lett. 1984, 25, 117. (d) Avramovitch, B.; Weyerstahl, P.; Rappoport, Z. J. Am. Chem. Soc. 1987, 109, 6687. (e) Hoz, S.; Basch, H.; Wolk, J. L.; Rappoport, Z.; Goldberg, M. J. Org. Chem. 1991, 56, 5424.
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17. Cabaret, D.; Maigret, N.; Welvart, Z.; Onong, K. N. V.; Gaudemer, A. J. Am. Chem. Soc. 1984, 106, 2870.
18. Beit-Yannai, M.; Rappoport, Z. J. Org. Chem. 1996, 61, 3553.
19. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New York, 1991; p 215.
20. The authors have deposited the atomic coordinates for E-1 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
21. Avramovitch, B.; Rappoport, Z. J. Am. Chem. Soc. 1988, 110, 911.
22. Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309.