A chemoselective route to either 4-methyl-2,4-diphenyl-2-pentene or 1,1,3-trimethyl-3-phenylindane from 2-phenylpropan-2-ol mediated by BiBr 3: A mechanistic study

Tetrahedron Letters

Volumn 51, Issue 32, 2010, Pages 4208-4210

  Howard, Fredrick ^a   Sawadjoon, Supaporn ^a   Samec, Joseph S M ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLSTYRENE; 1,1,3 TRIMETHYL 3 PHENYLINDANE; 2 PHENYLPROPAN 2 OL; 4 METHYL 2,4 DIPHENYL 2 PENTENE; BENZENE DERIVATIVE; BISMUTH BROMIDE; BISMUTH DERIVATIVE; INDAN DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 77955308934     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.018     Document Type: Article

References (21)

1. A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions 2004 Wiley-VCH Weinheim
2. R.A. Sheldon, I. Arends, U. Hanefeld, Green Chemistry and Catalysis 2007 Wiley-VCH Weinheim
3. B. Chaudhuri Org. Process Res. Dev. 3 1999 220 223
4. B. Chaudhuri, and M.M. Sharma Ind. Eng. Chem. Res. 28 1989 1757 1763
5. Q. Cai, J. Li, F. Bao, and Y. Shan Appl. Catal., A: Gen. 279 2005 139 143
6. H.-B. Sun, B. Li, R. Hua, and Y. Yin Eur. J. Org. Chem. 2006 4231 4236
7. M. Higashimura, K. Imamura, Y. Yokogawa, and T. Sakakibara Chem. Lett. 33 2004 728 729
8. N.H. Werstiuk, and G. Timmins Can. J. Chem. 66 1988 2309 2312
9. Kirk-Othmer Encyclopedia of Chemical Technology Vol. 21 1978 Wiley Interscience New York p 819
10. G. Stavber, M. Zupan, and S. Stavber Tetrahedron Lett. 47 2006 8463 8466
11. S. Stavber, and M. Zupan Tetrahedron Lett. 34 1993 4355 4356
12. R. Sanz, A. Martinez, V. Guilarte, J.M. Alvarez-Gutierrez, and F. Rodriguez Eur. J. Org. Chem. 2007 4642 4645
13. R. Sanz, A. Martinez, D. Miguel, J.M. Alvarez-Gutierrez, and F. Rodriguez Adv. Synth. Catal. 348 2006 1841 1845
14. B. Boyer, E.-M. Keramane, J.-P. Roque, and A.A. Pavia Tetrahedron Lett. 41 2000 2891 2894
15. E.-M. Keramane, B. Boyer, and J.-P. Roque Tetrahedron 57 2001 1917 1921
16. 4 without any difference in the outcome.
17. 3.
18. 3 were active as catalysts in this transformation.
19. In the proposed mechanism, enantioenriched phenylethanol and menthol were used. See Ref. 9.
20. 3.
21. R.C. Tolman The Principles of Statistical Mechanics 1938 Oxford University Press London, UK