Lewis acid-catalyzed rearrangement of multi-substituted arylvinylidenecyclopropanes

Journal of the American Chemical Society

Volumn 127, Issue 42, 2005, Pages 14552-14553

  Xu, Guang Cai ^a   Liu, Le Ping ^b   Lu, Jian Mei ^b   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; LEWIS ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; FRIEDEL CRAFTS REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

BORON; CATALYSIS; CYCLOPROPANES; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; TIN; ZIRCONIUM;

EID: 27144507457     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054988e     Document Type: Article

References (19)

1. (a) Poutsma, M. L.; Ibarbia, P. A. J. Am. Chem. Soc. 1971, 93, 440.
2. (b) Smadja, W. Chem. Rev. 1983, 83, 263.
3. (c) Hendrick, M. E.; Hardie, J. A.; Jones, M., Jr. J. Org. Chem. 1971, 36, 3061.
4. (d) Sugita, H.; Mizuno, K.; Saito, T.; Isagawa, K.; Otsuji, Y. Tetrahedron Lett. 1992, 33, 2539.
5. (e) Mizuno, K.; Sugita, H.; Kamada, T.; Otsuji, Y. Chem. Lett. 1994, 449 and references therein,
6. (f) Sydnes, L. K. Chem. Rev. 2003, 103, 1133.
7. For synthesis of vinylidenecyclopropanes, please see: (a) Isagawa, K.; Mizuno, K.; Sugita, H.; Otsuji, Y. J. Chem. Soc., Perkin Trans, 1 1991, 2283 and references therein,
8. (b) Al-Dulayymi, J. R.; Baird, M. S. J. Chem. Soc., Perkin Trans. 1 1994, 1547. The other papers related to vinylidenecyclopropanes:
9. (c) Maeda, H.; Hirai, T.; Sugimoto, A.; Mizuno, K. J. Org. Chem. 2003, 68, 7700.
10. (d) Pasto, D. J.; Brophy, J. E. J. Org. Chem. 1991, 56, 4556.
11. (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145.
12. (b) Xu, B.; Shi, M. Org. Lett. 2003, 5, 1415.
13. (c) Shi, M.; Xu, B.; Huang, J.-W. Org. Lett. 2004, 6, 1175.
14. (d) Shi, M.; Shao, L.-X.; Xu, B. Org. Lett. 2003, 5, 579.
15. Xu, G.-C; Ma, M.; Liu, L.-P.; Shi, M. Synlett 2005, 1869.
16. For isomerization of alkenylidenecyclopropanes catalyzed by Lewis acids, see: Fitjer, L. Angew. Chem., Int. Ed. Engl. 1975, 14, 360.
17. (a) Dicoordinated Carbocations: Rappoport, Z.; Stang, P. J., Eds.; John Wiley & Sons: New York, 1997; pp 137-138.
18. (b) Olah, G. A.; Reddy, V. P.; Prakash, G. K. S. Chem. Rev. 1992, 92, 69.
19. For the mechanism of the 1,3-proton shift, please see: Carey, F. A.; Sundburg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1990; pp 609-613.