Preparation of CF3-containing 1,3-Di- and 1,1,3-trisubstituted allenes

Journal of Organic Chemistry

Volumn 71, Issue 16, 2006, Pages 6251-6253

  Yamazaki, Takashi ^a   Yamamoto, Takahiro ^a   Ichihara, Ritsuko ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE COMPOUNDS; IODINE COMPOUNDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

HYDROXYL GROUPS; STEREOSPECIFIC MANNERS; TRISUBSTITUTION PATTERNS; VINYLIC IODIDES;

OLEFINS;

1,3 BUTADIENE; 4,4,4 TRIFLUORO 1 (1 NAPHTHYL) 2,3 BUTADIENE; 4,4,4 TRIFLUORO 1 (1 NAPHTHYL)BUT 2 YN 1 OL; 4,4,4 TRIFLUORO 2 IODO 1 (1 NAPHTHYL)BUT 2 EN 1 OL; ALLENE DERIVATIVE; HYDROXYL GROUP; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ZINC;

ACETYLATION; ARTICLE; CHEMICAL MODIFICATION; ELIMINATION REACTION; FLUORINATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33746885539     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060909l     Document Type: Article

References (20)

1. (a) Smart, B. E. J. Fluorine Chem. 2001, 109, 3.
2. (b) Hiyama, T. Organofluorine Compounds. Chemistry and Applications; Springer-Verlag: Berlin, Germany, 2000.
3. (c) Kitazume, T.; Yamazaki, T. Experimental Methods in Organic Fluorine Chemistry; Kodansha, Gordon and Breach: Tokyo, Japan, 1998.
4. (d) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; p 57.
5. For the preparation of allenes, see the following recent reviews. (a) Krause, N.; Hoffmann-Röder, A. Tetrahedron 2004, 60, 11671.
6. (b) Sydnes, L. K. Chem. Rev. 2003, 103, 1133.
7. For the synthetic application of allenic compounds, see: Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12.
8. (a) Mae, M.; Hong, J.-A.; Xu, B.; Hammond, G. B. Org. Lett. 2006, 8, 479.
9. (b) Ogu, K.; Akazome, M.; Ogura, K. J. Fluorine Chem. 2004, 125, 429.
10. (c) Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Collect. Czech. Chem. Commun. 2002, 67, 1421.
11. (d) Shen, Q.-L.; Hammond, G. B. J. Am. Chem. Soc. 2002, 124, 6534.
12. (e) Burton, D. J.; Hartgraves, G. A.; Hsu, J. Tetrahedron Lett. 1990, 31, 3699.
13. (f) Dolbier, W. R., Jr.; Burkholder, C. R.; Piedrahita, C. A. J. Fluorine Chem. 1982, 20, 637.
14. (a) Mizutani, K.; Yamazaki, T.; Kitazume, T. J. Chem. Soc., Chem. Commun. 1995, 51.
15. (b) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1995, 60, 6046.
16. See also the following: Katritzky, A. R.; Qi, M.; Wells, A. P. J. Fluorine Chem. 1996, 80, 145.
17. Qing, F.-L.; Gao, W.-Z.; Ying, J.-W. J. Org. Chem. 2000, 65, 2003.
18. Transformation of vinyl iodide to the corresponding organo-magnesium species with the methyl protection of the OH group was affected by the elimination to give the allenes. Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. J. Am. Chem. Soc. 1990, 112, 8042.
19. TMSCl was sometimes used as an activator of the Reformatsky reaction. See, for example: Ikegami, R.; Koresawa, A.; Shibata, T.; Takagi, K. J. Org. Chem. 2003, 68, 2195.
20. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, UK, 1988; p 360.