Tetrahedron

On the regioselectivity of the fremy's salt oxidation of phenols

PM Deya, M Dopico, AGRJ Morey, JM Saa

Index: Deya, Pedro M.; Dopico, Mercedes; Raso, Angel Garcia; Morey, Jeronimo; Saa, Jose M. Tetrahedron, 1987 , vol. 43, # 15 p. 3523 - 3532

Full Text: HTML

Citation Number: 27

Abstract

A detailed study of the regioselectivity of the Fremy's salt oxidation of phenols, including a series of MNDO calculations of the intermediate phenoxy radicals, has been carried out. The analysis of these results has led us to establish a new rule for the para vs. ortho regioselectivity, namely:“C-4 unsubstituted phenols, as well as phenols substituted at C-4 with easy-to-displace groups, undergo oxidation (or oxidative degradation) by the action ...

Related Articles:

Oxidation of Methoxy-and/or Methyl-Substituted Benzenes and Naphthalenes to Quinones and Phenols by H 2 O 2 in HCOOH

[Orita, Hideo; Shimizu, Masao; Hayakawa, Takashi; Takehira, Katsuomi Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 5 p. 1652 - 1657]

Oxidation of Methoxy-and/or Methyl-Substituted Benzenes and Naphthalenes to Quinones and Phenols by H 2 O 2 in HCOOH

[Orita, Hideo; Shimizu, Masao; Hayakawa, Takashi; Takehira, Katsuomi Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 5 p. 1652 - 1657]

Synthesis and Spectroscopic Characterization of [1′??14C] Ubiquinone??2,[1′??14C]??5??Demethoxy??5??hydroxyubiquinone??2, and [1′??14C]??5?? …

[Van Der Klei, Anita; De Jong, Robertus L. P.; Lugtenburg, Johan; Tielens, Aloysius G. M. European Journal of Organic Chemistry, 2002 , # 17 p. 3015 - 3023]

Oxidation of Methoxy-and/or Methyl-Substituted Benzenes and Naphthalenes to Quinones and Phenols by H 2 O 2 in HCOOH

[Orita, Hideo; Shimizu, Masao; Hayakawa, Takashi; Takehira, Katsuomi Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 5 p. 1652 - 1657]

Total synthesis of 20-norsalvinorin A. 1. Preparation of a key intermediate

[Takizawa, Yasuomi; Iwasa, Yoshihito; Suzuki, Toshiaki; Miyaji, Hiroyuki Chemistry Letters, 1993 , # 11 p. 1863 - 1864]

More Articles...