Abstract
Moderate yields of benzaldehyde, benzyl alcohol and benzylamine are obtained by the biomimetic oxidation of N-nitrosodibenzylamine with molecular oxygen catalysed by water soluble anionic manganese(III) 5,10,15,20-tetraphenylporphyrin acetate/sodium dithionite/methylene blue in aerosol-OT (AOT) reverse micelles, under phase transfer conditions with AOT concentration higher than 10−3M. The formation of α-hydroxy-N-nitrosodibenzylamine and its decomposition products, benzaldehyde and benzyl alcohol in reverse micellar systems are governed by the ratio of water and AOT, pH and other changes in the microenvirpnment.
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Baciocchi E, Crescenzi M and Lanzalunga O 1990J. Chem. Soc., Chem. Commun. 687
Band S, Maiocchi A, Moggi A, Montanari F and Quici S 1990J. Chem. Soc., Chem. Commun. 1794
Briffraud T, Larpent C and Patin H 1990J. Chem. Soc., Chem. Commun 1193
Battioni P, Bartoli J F, Leduc P, Fontecave M and Mansuy D 1987J. Chem. Soc., Chem. Commun. 791
Chauhan S M S, Kohli T S, Rao K V and Gulati A 1990Indian J. Chem. B29 539
Coulson C J, Kind D J and Wiseman A 1984Trends Biochem. Sci. 9 446
Duncan I A, Harriman A and Porter G 1980J. Chem. Soc., Faraday Trans. II 1415
Erjomin A N and Metelitza D I 1983Biochim. Biophys. Acta 732 377
Esch J, Roks M F M and Nolte R J M 1986J. Am. Chem. Soc. 108 6093
Fendler J H 1987Chem. Rev. 87 877
Fleischer E B, Palmer J M, Srivastava T S and Chatterjee A 1971J. Am. Chem. Soc. 93 3162
Fraser R R and Ng L K 1976J. Am. Chem. Soc. 98 5895
Guengrich F P and Macdonald T L 1984Acc. Chem. Res. 17 9
Hall P F 1985Vitamin and Hormones 42 315
Hall P F 1986Steroids 48 131
Harriman A and Porter G 1979J. Chem. Soc., Faraday Trans II 1532
Helenius A and Simons K 1975Biochim. Biophys. Acta 415 29
Holm R H 1987Chem. Rev. 87 1401
Ingelman-Sundberg M, Haaparanta T and Rydstrom J 1981Biochemistry 20 4100
Jorgenson K A 1989Chem. Rev. 89 431
Kunz B C, Rehorek M, Hauser H, Winterhalter K H and Richter C 1985Biochemistry 24 2889
Kurihara K and Fendler J H 1983J. Am. Chem. Soc. 105 6152
Lindsey-Smith J R, Nee M W, Noar J B and Bruice T C 1984J. Chem. Soc., Perkin II 225
Lindsey-Smith J R and Mortimer D N 1986J. Chem. Soc. Perkin II 1743
Looney C E, Phillips W D and Reilly E L 1957J. Am. Chem. Soc.,79 6136
Luisi P L 1985Angew. Chem., Int. Ed. Engl. 24 439
Luisi P L and Magid L J 1986CRC Crit. Rev. Biochem. 409 20
Magid L, Walde P, Zampieri G, Battistel E, Peng Q, Trotta E, Maestro M and Luisi P L 1988Colloids Surf. 30 193
Mansuy D 1987Pure Appl. Chem. 59 759
Mansuy D, Battioni P and Battioni J P 1989Eur. J. Biochem. 184 267
Martinek K, Levashov A V, Klyachko N, Khemelnitski Y L and Berezin I V 1986Eur. J. Biochem. 155 453
Nebert D W and Gonzalez F J 1987Annu. Rev. Biochem. 56 945
Nagalsu Y, Higuchi T and Hirobe M 1990Chem. Pharmcol. Bull. 38 400
Pshezhetskii A V, Merker Sh, Klyachko N L, Pepanyan G S, Martinek K and Levashov A V 1987Biokhimiya 53 1013
Ringsdorf H, Schlarb B and Venzmer J 1988Angew. Chem. Int. Ed. Engl. 27 113
Ranganathan D, Singh G P and Ranganathan S 1989J. Am. Chem. Soc.,111 1144
Sjngh A K, Sandorfy C and Fendler J H 1990J. Chem. Soc., Chem. Commun. 233
Srivastava T S and Tsutsui M 1973J. Org. Chem. 38 2103
Tabushi I and Kodera M 1986J. Am. Chem. Soc. 108 1101
Tabushi I 1988Coordination Chem. Rev. 86 1
Taniguchi H, Imai Y and Sato R 1987Biochemistry 26 7084
White P W 1990Bioorg. Chem. 18 440
Walde P, Peng Q, Fandavis N W, Ballistel E and Luisi P L 1988Eur. J. Biochem. 173 401
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Chauhan, S.M.S., Satapathy, S. Biomimetic oxidation of N-nitrosodibenzylamine with molecular oxygen catalysed by chemical cytochrome P-450 in AOT reverse micelles. Proc. Indian Acad. Sci. (Chem. Sci.) 103, 645–653 (1991). https://doi.org/10.1007/BF02841066
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DOI: https://doi.org/10.1007/BF02841066