Photooxidation of methyldithiepins into dithiepin carboxaldehydes in carbon tetrachloride

Organic Letters

Volumn 1, Issue 6, 1999, Pages 937-939

  Wan, Yongqin ^a   Barnhurst, Loren A ^a   Kutateladze, Andrei G ^a  

^a UNIVERSITY OF DENVER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000955429     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990870p     Document Type: Article

References (17)

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3. Most notably, such ET-initiated cleavages are used for photochemical deprotection of dithioacetals: (a) Schmittel, M.; Levis, M. Synlett 1996, 315-316.
4. (b) Tanemura, K.; Dohya, H.; Imamura, M.; Suzuki, T.; Horaguchi, T. Chem. Lett. 1994, 965-8.
5. (c) Kamata, M.; Murakami, Y.; Tamagawa, Y.; Kato, M.; Hasegawa, E. Tetrahedron 1994, 50, 12821-8.
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7. (e) Epling, G. A.; Wang, Q. Synlett 1992, 335-6.
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9. All photooxidations were carried out with a medium-pressure Hg UV source in Pyrex tubes with bubbling oxygen. A 10 mM amount of 1a-g in carbon tetrachloride was used, and irradiations were carried out until complete conversion of the starting material was achieved.
10. For a review, see: Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357-402.
11. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1990, 55, 1061-1065 and references therein.
12. Alfassi, Z. B.; Mosseri S. J. Phys. Chem. 1984, 88, 3296-3300.
13. Battino, R. Solubility Data Series: Vol. 7, Oxygen and Ozone; Pergamon: Oxford, England, 1981.
14. Nicholas, A. M. d. P.; Arnold, D. R. Can. J. Chem. 1982, 60, 2165-2179
15. Eriksen J.; Foote C. S.; Parker T. L. J. Am. Chem. Soc. 1977, 99, 6455-6456.
16. Desulfurization in a similar dithiine system has recently been carried out with Raney-Ni deactivated with acetic acid: Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. J. Org. Chem. 1997, 62, 9369-9371. In our case, this technique did not work and we utilized the Raney-Ni/acetone approach described in: Williams, J. R.; Tran, P. B. Synthesis 1988, 705-706.
17. Desulfurization in a similar dithiine system has recently been carried out with Raney-Ni deactivated with acetic acid: Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. J. Org. Chem. 1997, 62, 9369-9371. In our case, this technique did not work and we utilized the Raney-Ni/acetone approach described in: Williams, J. R.; Tran, P. B. Synthesis 1988, 705-706.