Generation of ketenes by photolysis of naphtho[1,8-de]-1,3- dichalcogeninylidene 1-oxides

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5211-5214

  Kobayashi, Kenji ^a   Shinhara, Satoshi ^a   Moriyama, Masaya ^b   Fujii, Takayoshi ^a   Horn, Ernst ^a   Yabe, Akira ^b   Furukawa, Naomichi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

Ketenes; Photochemistry; Selenium and compounds; Sulfur compounds

Indexed keywords

1 NAPHTHOL; 1 NAPHTHOL DERIVATIVE; KETENE DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; DEHYDRATION; INFRARED SPECTROSCOPY; IRRADIATION; PHOTOCHEMISTRY; PHOTOLYSIS;

EID: 0033538597     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00940-5     Document Type: Article

References (18)

1. Wagner, B. D.; Arnold, B. R.; Brown, G. S.; Lusztyk, J. J. Am. Chem. Soc. 1998, 120, 1827 and references therein.
2. Nakatani, K.; Shirai, J.; Sando, S.; Saito, I. J. Am. Chem. Soc. 1997, 119, 7626.
3. Furukawa, N. Bull. Chem. Soc. Jpn. 1997, 70, 2571.
4. (a) Fujihara, H.; Yabe, M.; Furukawa, N. J. Org. Chem. 1993, 58, 5291.
5. (b) Ouchi, A.; Koga, Y. J. Org. Chem. 1997, 62, 7376.
6. (a) Furukawa, N.; Fujii, T.; Kimura, T.; Fujihara, H. Chem. Lett. 1994, 1007.
7. (b) Fujii, T.; Kimura, T.; Furukawa, N. Tetrahedron. Lett. 1995, 36, 1075.
8. (c) Fujii, T.; Takahashi, O.; Furukawa, N. J. Org. Chem. 1996, 61, 6233.
9. Ku, B.; Oh, D.-Y. Synth. Commun. 1989, 19, 433-438.
10. 2: C, 47.48; H, 3.42. Found: C, 47.69; H, 3.38.
11. Stang, P. J.; Roberts, K. A.; Lynch, L. E. J. Org. Chem. 1984, 49, 1653.
12. w = 0.052 using 1501 unique reflections (I > 3.0o(1)).
13. (a) Glass, R. S.; Andruski, S. W.; Broeker, J. L.; Firouzabadi, H.; Steffen, L. K.; Wilson, G. S. J. Am. Chem. Soc. 1989, 111, 4036.
14. (b) Glass, R. S.; Broeker, J. L.; Firouzabadi, H. J. Org. Chem. 1990, 55, 5739.
15. Guo, Y.; Jenks, W. S. J. Org. Chem. 1995, 60, 5480-5486.
16. McMahon, R. J.; Abelt, C. J.; Chapman, O. L.; Johnson, J. W.; Kreil, C. L.; Leroux, J.-P.; Mooring, A. M.; West., P. R. J. Am. Chem. Soc. 1987, 109, 2456.
17. 14
18. Lin-Vien, D.; Cothup, N. B.; Fateley, W. G.; Graselli, J. G. The Handbook of Infrared and Roman Characteristic Frequencies of Organic Molecules; Academic: San Diego, 1991; ch. 13, p. 216.