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Synthesis and properties of group 15 element porphyrin peroxides

✍ Scribed by Wataru Satoh; Shuji Masumoto; Yohsuke Yamamoto; Kin-ya Akiba

Book ID
102227966
Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
349 KB
Volume
12
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

[(Por)M(R)(OOR′)]^+^Y^−^ (Por: TPP [tetraphenylporphyrin], OEP [octaethylporphyrin]; M: Sb, As, P; R: Me, Et, Ph; R′: H, C(=O)m‐ClC~6~H~4~, t‐Bu) were prepared from [(Por)M(R)(X)]^+^Y^−^ (X: OTf, Br). The reactivities of the peroxide porphyrins toward nucleophiles such as triphenylphosphine increased in the order of ‐OOt‐Bu, m‐CPBA, and ‐OOH derivatives. Phosphorus (P‐OOH) and arsenic hydroperoxide (As‐OOH) were much more reactive than the corresponding antimony hydroperoxide (Sb‐OOH). The higher reactivity of phosphorus and arsenic peroxides can be explained by the stability of the M=O (M=P, As) bonding system in the intermediates of the oxidation reactions. An X‐ray structural analysis of [(TPP)Sb‐(Me)(OOt‐Bu)]^+^PF~6~^−^ is presented. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:431–443, 2001

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