Metalation of iminium ions formed in the reaction of tertiary amines with TiCl4

Organic Letters

Volumn 1, Issue 6, 1999, Pages 857-859

  Bharathi, Pandi ^a   Periasamy, Mariappan ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001510055     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990745d     Document Type: Article

References (14)

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5. (e) Yoshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 8727 and references therein.
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7. (a) Periasamy, M.; Srinivas, G.; Bharathi, P. J. Org. Chem. 1999, 64, 4204.
8. (b) Bharathi, P.; Periasamy, M. Unpublished results.
9. 2 (2 x 25 mL). The combined organic extract was washed with brine solution (10 mL) and dried over anhydrous MgSO4. The solvent was removed, and the residue was chromatographed on a silica gel column. The unreacted benzaldehyde was eluted using 2:98 EtOAc/hexane mixture. The cinnamaldehyde was separated using 4:98 EtOAc/hexane mixture as eluent (0.607 g, 46%).
10. Antler, W., Lambengayer, A. W. J. Am Chem. Soc. 1955, 77, 5250.
11. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principle and application of organotransition metal chemistry; University Science Books: Mill Valley, 1987; p 725.
12. (b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J.; Stephenson, D. K. J. Chem. Res. (S) 1984, 360.
13. Leonard, N. J.; Hay, A. S.; Fulmer, R. W.; Gash, V. W. J. Am. Chem. Soc. 1955, 77, 439.
14. + (elm) 262.