Journal of Molecular Catalysis A: Chemical 171 (2001) 115–121 Cytochrome P-450 model reactions: a kinetic study of epoxidation of alkenes by iron phthalocyanine Nasser Safari ∗ , Farzad Bahadoran Chemistry Department, Shahid Beheshti University, P.O. Box 19397-4716, Evin, Tehran, Iran Abstract A kinetic study for measuring the relative rate of the catalytic epoxidation of various alkenes has been employed based upon the disappearance of the 1,4-diphenylbutadiene. Iron(III) phthalocyanine chloride as catalyst, imidazole as cocatalyst, iodosylbenzene as oxygen donor and a mixture of dichloromethane, methanol, water (80:18:2) as solvent, were used for achieving to a homogeneous system. Effects of nitrogen donor bases such as pyridine, piperidine and collidine on the yield of alkenes epoxidation were investigated and possibility of the same mechanism for iron phthalocyanine and porphyrin has been demonstrated. © 2001 Elsevier Science B.V. All rights reserved. Keywords: Iron phthalocyanine; Alkene epoxidation; Kinetic; Relative rate 1. Introduction The epoxidation of alkenes catalyzed by transition metals is a field, which extensively has been devel- oped during last two-decades [1,2]. Among them, metalloporphyrins in oxidation of substrates with var- ious single-oxygen atom donors have had a major role for understanding of biological related reaction of cytochrome P-450, where oxo-metalloporphyrins are accepted as reactive intermediate [3–6]. Phthalocya- nine with a similar structure to the porphyrin has intensively been investigated in numbers of areas such as industrial colorants and electrophotogra- phy, photoconductors, nonlinear optic, optical data storage, photodynamic therapy of cancer, fuel cell, chemical sensor, etc. [7–10]. Moreover, Larsen and Jorgensen [11] have reported that manganese and iron phthalocyanines are among the most effective ∗ Corresponding author. E-mail address: n-safari@cc.sbu.ac.ir (N. Safari). metallophthalocyanines for alkenes epoxidation when iodosylbenzene were employed as the oxy- gen donor. Banfi et al. [12] have compared reac- tivity of Mn-octanitrophthalocyanine with different Mn-porphyrins where peracetic acid was oxygen donor and concluded that Mn-phthalocyanine have comparative catalytic activity to tetra phenyl por- phyrin iron(III) chloride. Nappa and Tolman [13] have reported that perfluorinated FePc catalyzed the oxidation of cyclohexane by iodosylbenzene and El- lis and Lyons [14] have shown that the N 3 - ligand has promotional effect on catalytic hydroxylation of alkanes by metallophthalocyanines. Hadasch and Meunier [15] have recently reported that water solu- ble iron tetrasulfophthalocyanine is effective catalyst for oxidation of aromatic compounds. In spite of similarity between metallophthalocya- nines and metalloporphyrins, the latter has played an important role in understanding the mechanism of oxidation catalyzed by cytochrome P-450 [3], however, metallophthalocyanines have not been 1381-1169/01/$ – see front matter © 2001 Elsevier Science B.V. All rights reserved. PII:S1381-1169(01)00077-2