Mechanistic aspects of the C-H alkynylation reaction of acetylenic triflones. Determination of phenyl versus cyclohexyl migratory aptitude for a vinylidine carbene

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5269-5272

  Xiang, Jason S ^a   Fuchs, P L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030598081     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01117-3     Document Type: Article

References (17)

1. 1 Syntheses Via Vinyl Sulfones 67. Triflones 6.
2. 2 Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486.
3. 3 "Handbook of Chemistry and Physics," 74th Edition, 1993-1994, 9-137, D. R. Lide, Ed.
4. 4 Stang, P. J. Chem. Rev. 1978, 78, 383.
5. 5 An addition-elimination mechanism which features addition of cyclohexyl radical to the α-carbon of β-phenylethynyl phenylsulfone to produce compound 5 has been previously proposed: Russell, G. A.; Ngoviwatchai, P. J. Org. Chem. 1989, 54, 1836; and references cited therein.
6. 6 (a) Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1992, 33, 1291;
7. (b) Hu, C.-M.; Qing, F. -L.; Huang, W. -Y. J. Org. Chem. 1991, 56, 2801;
8. (c) Huang, W. -Y.; Hu, L. -Q. J. Fluorine Chem. 1989, 44, 25;
9. (d) Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1991, 32, 7525.
10. 7 Medebielle, M.; Pinson, J.; Saveant, J.-M. J. Am. Chem. Soc. 1991, 113, 6872.
11. 8 Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
12. 9 Corey, E.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.
13. 10 (a) Traficante, D. D.; Maciel, G. E., J. Phys. Chem. 1965, 69, 1348;
14. (b) Izawa, K.; Okuyama, T.; Fueno, T. Bull. Chem. Soc. Jpn. 1973, 46, 2881.
15. 11 Cyclohexyl migration is preferred over phenyl migration by 71:14 in the Baeyer-Villiger reaction of phenyl cyclohexyl ketone: Friess, S. L.; Franham, N. J. Am. Chem. Soc. 1950, 72, 5518.
16. 12 Many ketones react poorly with this reagent: Topolski, M. J. Org. Chem. 1995, 60, 5588, and references therein.
17. 13 Hedhli, A.; Chaabouni, M. M.; Baklouti, A. J. Fluorine Chem. 1992, 56, 239.