New synthetic method of benzaldehydes and α,β-unsaturated aldehydes with I2 under photoirradiation

Chemistry Letters

Volumn , Issue 7, 2001, Pages 686-687

  Itoh, Akichika ^a   Kodama, Tomohiro ^a   Masaki, Yukio ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035596167     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.686     Document Type: Article

References (11)

1. F. A. Carey and R. J. Sundberg, "Advanced Organic Chemistry: Reactions and Synthesis", Plenum Pub Corp., New York (1990).
2. "Comprehensive Organic Transformations: A Guide to Functional Group Preparations," ed. by R. C. Larock, Wiley-VCH, New York (1989).
3. A. J. Fatiadi, Synthesis, 65, 133 (1976) and see the references cited therein.
4. In the presence of iodine, alcohols are oxidized by electrochemical method or metals: Z. Ogumi, S. Ohashi, Z. Takehara, Electrochim. Acta, 30, 121 (1985); Y. N. Kukushkin, V. N. Demidov, N. P. Fedyanin, Zh. Obshch. Khim., 53, 2393 (1983); M. L. Mihailovic, Z. Cekovic, J. Stankovic, J. Chem. Soc. D, 1969, 981.
5. In the presence of iodine, alcohols are oxidized by electrochemical method or metals: Z. Ogumi, S. Ohashi, Z. Takehara, Electrochim. Acta, 30, 121 (1985); Y. N. Kukushkin, V. N. Demidov, N. P. Fedyanin, Zh. Obshch. Khim., 53, 2393 (1983); M. L. Mihailovic, Z. Cekovic, J. Stankovic, J. Chem. Soc. D, 1969, 981.
6. In the presence of iodine, alcohols are oxidized by electrochemical method or metals: Z. Ogumi, S. Ohashi, Z. Takehara, Electrochim. Acta, 30, 121 (1985); Y. N. Kukushkin, V. N. Demidov, N. P. Fedyanin, Zh. Obshch. Khim., 53, 2393 (1983); M. L. Mihailovic, Z. Cekovic, J. Stankovic, J. Chem. Soc. D, 1969, 981.
7. 4 and concentrated under reduced pressure. Pure product was obtained after purification by preparative TLC. 6 5 was recovered in 8% after 24 h.
8. 2 (2 equiv) was not effective: the yield of 6 was reduced and 18% of 5 was recovered after 24 h.
9. 2 column chromatography.
10. F. B. Mallory and C. W. Mallory, Org. React., 30, 1 (1984).
11. We believe that iodine is re-produced in situ, since the dark brown color of the reaction mixture seemed to remain unchanged as such.