DDQ-promoted functionalization of phenylalkylacetylenes at the propargylic carbon

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 8035-8037

  Montevecchi, Pier Carlo ^a   Navacchia, Maria Luisa ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001384304     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980966h     Document Type: Article

References (24)

1. Oxidations of activated G-H bonds have been extensively reviewed. See: (a) Hudlicky M. Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington, DC, 1990.
2. (b) Bulman Page, P. C.; McCarthy, T. J. Oxidation Adjacent to C=C Bonds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 7, Chapter 2.1.
3. For electrochemical oxidations of hydrocarbons, see: Lund, H.; Baizer, M. M. Organic Electrochemistry, 3rd ed.; Marcel Dekker: New York, 1991.
4. Chabaud, B.; Sharpless, K. B. J. Org. Chem. 1979, 44, 4202.
5. Montevecchi, P. C.; Navacchia, M. L. J. Org. Chem. 1997, 62, 5600.
6. Montevecchi, P. C.; Navacchia, M. L. J. Org. Chem. 1998, 63, 537 and references therein.
7. A class of insect pheromones belongs to the conjugated enynes family; see: Mori, K. The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley: New York, 1992; Vol. 9.
8. Normant, J. F. Mod. Synth. Methods 1983, 3, 139.
9. Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349.
10. 2 and sp Carbon Centers. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, Chapter 2.4.2.
11. Clough, J. M. The Ramberg-Backlund Rearrangement. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, Chapter 3.8.9.
12. Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153.
13. Foster, R.; Foreman, M. In The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; John Wiley and Sons: New York, 1974; Part 1, pp 257-423.
14. Fu, P. P.; Harvey, R. G. Chem. Rev. 1978, 78, 317.
15. Capella, L.; Montevecchi, P. C.; Nanni, D. J. Org. Chem. 1994, 59, 7379.
16. Peover, M. E. J. Chem. Soc. 1962, 4540.
17. ̇- counterion. Instead, covalent complexes between quinones and diarylacetylenes are formed under photochemical conditions in the solid state; see: Bosch, E.; Hubig, S. M.; Lindeman, S. V.; Kochi, J. K. J. Org. Chem. 1998, 63, 592.
18. We also found that, under our conditions, allylic alcohols such as 1-octen-3-ol can be oxidized by DDQ to the corresponding aldehydes in good yields. The DDQ oxidation of allylic alcohols has been already reported in a few cases (see: Braude, E. A.; Linstead, R. P.; Wooldridge, K R. J. Chem. Soc. 1956, 3070.
19. Burn, D.; Petrow, V.; Weston, G. O. Tetrahedron Lett. 1960, 14).
20. Ward, H. R. J. Am. Chem. Soc. 1967, 89, 5517.
21. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
22. Alami, M.; Fern, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403.
23. Casson, S.; Kocienski, P.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301.
24. Noro, M.; Masuda, T.; Ichimura, A. S.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1994, 116, 6179.