Tetrahedron letters

Oxidation of catechol and of 2, 6-di-tert-butylphenol by dioxiranes

A Altamura, C Fusco, L D'Accolti, R Mello, T Prencipe…

Index: Altamura; Fusco; D'Accolti; Mello; Prencipe; Curci Tetrahedron Letters, 1991 , vol. 32, # 40 p. 5445 - 5448

Full Text: HTML

Citation Number: 25

Abstract

Abstract In a biomimetic transformation, the selective oxidation of catechol (2) to Z, Z- muconic acid (3) has been achieved under extremely mild conditions using methyl (trifluoromethyl) dioxirane (1b). Both dioxirane 1b and dimethyldioxirane (1a) have been applied to the oxidation of 2, 6-di-tert-butylphenol (4); the product natures suggest the incursion of radical pathways.

Related Articles:

Catalytic oxidation of phenols to p-quinones with the hydrogen peroxide and methyltrioxorhenium (VII) system

[Adam, Waldemar; Herrmann, Wolfgang A.; Lin, Jianhua; Saha-Moeller, Chantu R. Journal of Organic Chemistry, 1994 , vol. 59, # 26 p. 8281 - 8283]

Oxygenase model reactions. 1. Intra-and extradiol oxygenations of 3, 5-di-tert-butylcatechol catalyzed by (bipyridine)(pyridine) iron (III) complex

[Funabiki,T.; Mizoguchi,A.; Sugimoto,T. Journal of the American Chemical Society, 1986 , vol. 108, p. 2921]

Extradiol oxygenation of 3, 5-di-tert-butylcatechol with O2by iron chlorides in tetrahydrofuran–water as a model reaction for catechol-2, 3-dioxygenases

[Funabiki, Takuzo; Yoneda, Izumi; Ishikawa, Michiya; Ujiie, Mikio; Nagai, Yasutaka; Yoshida, Satohiro Journal of the Chemical Society, Chemical Communications, 1994 , # 12 p. 1453 - 1454]

More Articles...