Solvent directed electrophilic iodination and phenylselenenylation of activated alkyl aryl ketones

Tetrahedron Letters

Volumn 44, Issue 49, 2003, Pages 8753-8756

  Panunzi, Barbara ^a   Rotiroti, Lucia ^a   Tingoli, Marco ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

2,2 dimethoxyketones; Hypervalent iodine; Iodine; Selenium

Indexed keywords

CARBONYL DERIVATIVE; IODINE; IODINE DERIVATIVE; KETONE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL MODIFICATION; GAS CHROMATOGRAPHY; IODINATION; MASS SPECTROMETRY; PHENYLSELENENYLATION;

EID: 0242361248     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.037     Document Type: Article

References (17)

1. Tingoli M., Tiecco M., Testaferri L., Temperini A. Synth. Commun. 28:1998;1769-1778.
2. De Corso A.R., Panunzi B., Tingoli M. Tetrahedron Lett. 42:2001;7245-7247.
3. D'Auria M., Mauriello G. Tetrahedron Lett. 36:1995;4883-4884.
4. Tiecco M., Testaferri L., Bagnoli L., Marini F., Temperini A., Tomassini C., Santi C. Tetrahedron Lett. 56:2000;3255-3260.
5. Stavber S., Jereb M., Zupan M. Chem. Commun. 2002;488-489.
6. Jereb M., Stavber S., Zupan M. Synthesis. 2003;853-858.
7. Buchwald S.L., Watson B.T., Lum R.T., Nugent W.A. J. Am. Chem. Soc. 109:1987;7137-7141.
8. +) (5), 161 (10), 118 (10), 104 (28), 91 (100), 63 (60).
9. Smith D.S., Winnick J., Ding Y., Bottomley L.A. Electrochim. Acta. 43:1998;335-339.
10. Bringmann G., Geisler J.P. Synthesis. 1989;608-610.
11. In the reaction of 2′,4′-dimethoxyacetophenone compound 5d was consumed and partially phenylselenenylated on the aromatic ring (<10%).
12. Tiecco M., Testaferri L., Tingoli M., Bartoli D. J. Org. Chem. 55:1990;4523-4528.
13. Szmant H.H., Nanjundiah R. Org. Prep. Proced. Int. 9:1977;35-38.
14. Abbaspou Tehrani K., Boeykens M., Tyvorskii V.I., Kulinkovich O., De Kimpe N. Tetrahedron. 56:2000;6541-6548.
15. Carre M.C., Gregoire B., Caubere P. J. Org. Chem. 49:1984;2050-2052.
16. Tiecco M., Testaferri L., Tingoli M., Bartoli D., Marini F. J. Org. Chem. 56:1991;5207-5210.
17. Tanabe Y., Mitarai K., Higashi T., Misaki T., Nishii Y. Chem. Commun. 2002;2542-2543.