Decahydronaphthalene oxidation

MODEL STUDIES ON HEME MONOOXYGENASES Table 5. Fe porphyrin catalyzed cw-decahydronaphthalene oxidation [46,189] ... 

Explosions due to the presence of peroxides formed by aerial oxidation of ethers and tetrahydrofuran, decahydronaphthalene, acrylonitrile, styrene and related compounds. 

It must be stored out of contact with air to avoid the formation of explosive (per-oxidic) compounds [1]. The sodium salt is a safe source of butenyne for synthetic use [2], Explosive properties of the liquid and gaseous hydrocarbon alone, or diluted with decahydronaphthalene, were determined [3], Mechanical failure of a compressor circulating the gaseous hydrocarbon through a reaction system led to local... 

Additive. Addition of an atom or group of atoms, e.g., pyridine A-oxide, and decahydronaphthalene... 

Toluene diisocyanate was distilled through a spinning band column. After a small forecut, distillation proceeded smoothly at 80°C (1.3 mm Hg). Polymerization of a 10% solution in boiling decahydronaphthalene was carried out with catalytic quantities of l-ethyl-3-methyl-3-phospholene oxide. The reaction was... 

Oxidation of cis-decahydronaphthalene with chloro(5,10,15,20-tetraarylporphyri-nato)iron(III) in the presence of the oxygen transfer agent PhIO, also gives a stereospecific... 

DEB-M. See Diethylboron methoxide Debricin. SeeFicin DEC. See Diethyl carbonate Dec. See Decahydronaphthalene DECA Decabrom Decabrome. See Decabromodiphenyl oxide Decabromobiphenyl CAS 13654-09-6 Empirical BrioCi2 Uses Flame retardant Manuf./Distrib. Atofina SA http //www.atofina.com... 

Perhydrogeraniol. See 3,7-Dimethyl-1 -octanol Perhydrol-urea. See Urea peroxide Perhydronaphthalene. See Decahydronaphthalene cis-Perhydronaphthalene. See cis-Decalin Perhydrosqualene. See Squalane 97% HLS Periclase] 98% 1LS Periclase] 98% 3LS Periclase] Periclase 96/H-D/8-1] Periclase 97% HLS] Periclase 98/1-1] Periclase 98% 3LS] Periclase 98% ILS] Periclase. See Magnesium oxide... 

The catalytic system consisting of PhIO and various iron porphyrins hydroxylates unactivated alkanes under ambient conditions [83,88]. The substrates studied were cyclohexane, cycloheptane, adamantane, cis-decahydronaphthalene and norcarane, and the catalysts - Fe(TPP)Cl, Fe(TTP)Cl, Fe(TNP)Cl and Fe(TMP)Cl. Monohydroxylated products predominated in all cases, with maximum yields of 30-39 % based on PhIO. High selectivity for tertiary centers (adamantane), retention of configuration at carbon (cis-decaline), and a large kinetic isotope effect (12.9) have ben observed. The free radical trap bromotrichloromethane changes the product distribution, pointing to a radical mechanism. The mechanism (Scheme 4) is essentially the same as that proposed previously for alkane oxidation by cytochrome P-450 [89]. 

Hydroxylation of cis-decahydronaphthalene with Fe (TPP)Cl and iodosylbenzene produced mainly c/ -O-decanol (Table 5) [46, 189], indicating that the hydroxylation proceeds with retention of configuration at carbon. Chang and Ebina showed the oxidation of anisole by iodosylbenzene with Fe (TPP)Cl or Fe (TPFPP)Cl (TPFFP tetarkis(pentafluorophenyl)porphyrin) gave methoxyphenols with marked NIH shifts, comparable with those for microsomal systems [190]. At the same time, fluorinated porphyrin was found to be much a more efficient oxidation catalyst. Systematic study on the catalytic efficiency of halogenated metalloporphyrin will be discussed later. 

Kuo and Gregor (1983) have studied the applicability of such a relation for the solvent decahydronaphthalene (CioHia, decaUn) and the complexing agent trioctylphosphine oxide (TOPO) under conditions where the extent of dimerization was negligible (K2 = 0). Figure 5.2.7 shows the distribution coefficient, k" , of acetic acid with a fixed initial concentration (0.0893 M) as the TOPO concentration was varied from 0 to 0.52 M in decaUn. They had earlier observed that a value of K3 = 260 described the value of well when Ki = 0.024 for a = 0.1295 M. 

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