Electrophilic aromatic alkylation by hydroperoxides. Competition between ionic and radical mechanisms with phenols

Journal of Organic Chemistry

Volumn 64, Issue 24, 1999, Pages 8812-8815

  Liguori, Lucia ^a   Bjørsvik, Hans René ^b   Fontana, Francesca ^c   Bosco, Dino ^a   Galimberti, Laura ^a   Minisci, Francesco ^a  

^a POLITECNICO DI MILANO   (Italy)

^b UNIVERSITY OF BERGEN   (Norway)

^c UNIVERSITY OF BERGAMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROPEROXIDE; ION; PHENOL DERIVATIVE; RADICAL;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0033607465     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990742e     Document Type: Article

References (14)

1. Van Stevenik, A. W.; Kosymon, E. C. Recl. Trav. Chim. 1960, 79, 413.
2. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533; Science 1966, 45, 581.
3. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533; Science 1966, 45, 581.
4. Olah, G. A. Friedel-Crafts and Related Reactions; 1964; p 417.
5. Shimigu, I.; Khieu, M. K.; Nagatomo, M.; Nakajima, T.; Yamamoto, A. Chem. Lett. 1997, 851.
6. Fu, X.; He, M.; Lei, Q.; Luo, B. Synth. Commun. 1991, 21, 1273.
7. Walling, C. In Active Oxygen in Chemistry, SEARCH series, vol.2; Foote, C. S. Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic & Professional: London, 1995; p 24.
8. Olah, G. A.; Krishnamurti, R.; Surya, G. K. Compr. Org. Synth. 1991, 3, 293.
9. Perkins, M. J. Radical Chemistry; Ellis Horwood: New York, 1994; p 122.
10. ref 8, p 91.
11. 13C NMR: Yamamura, T.; Nishiwaki, K.; Tanigaki, Y.; Terauchi, S.; Tomiyama, S.; Nishiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 2955.
12. 13C NMR: Yamamura, T.; Nishiwaki, K.; Tanigaki, Y.; Terauchi, S.; Tomiyama, S.; Nishiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 2955.
13. 13C NMR: Yamamura, T.; Nishiwaki, K.; Tanigaki, Y.; Terauchi, S.; Tomiyama, S.; Nishiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 2955.
14. 13C NMR: Yamamura, T.; Nishiwaki, K.; Tanigaki, Y.; Terauchi, S.; Tomiyama, S.; Nishiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 2955.