NITROSAMINE CHEMISTRY 601 (21) W. Rolle, P. Gehlert and E. Renner, Kinetische Untersuchungen fiber die Bilding von Diethyl- nitrosamin aus Stickstoffoxiden und Diethylamin in der Gasphase, Z. Chem., 18, 99 (1978). (22) J. H. Ridd, Nitrosation, diazotization and deamination, Q. Rev. Chem. Soc., 15,418 (1961). (23) S.S. Mirvish, Formation of N-nitroso compounds. Chemistry, kinetics and in vivo occurrence, Toxicol. Appl. Pharmacol., 31,325 (1975). (24) S.S. Mirvish, Kinetics of dimethylamine nitrosation in relation to nitrosamine carcinogenesis, J. Nat. CancerInst., 44, 633 (1970). (25) B.C. Challis and S. A. Kyrtopoulos, Nitrosation under alkaline conditions, J. Chem. Sac., Chem. Cam- mun., 877 (1976). (26) B.C. Challis and S. A. Kyrtopoulos, Rapid formation of carcinogenic N-nitrosamines in aqueous al- kaline solutions, Br. J. Cancer, 35,693 (1977). (27) B.C. Challis, A. Edwards, R. R. Hunma, S. A. Kyrtopoulos and J. R. Outram, Rapid Formation of N- Nitrosamines from Nitrogen Oxides Under Neutral and Alkaline Conditions, in E. A. Walker, M. Castegnaro, L. Griciute and R. E. Lyle, "Environmental Aspects of N-Nitroso Compounds," IARC Scientific Publications no. 19, International Agency for Research on Cancer, Lyon, France, 1978, pp 127-142. (28) E. H. White, The chemistry of the N-alkyl-N-nitrosamides. I. Methods of preparation, J. Amer. Chem. Sac., 77, 6008 (1955). (29) E. H. White and W. R. Feldman, The nitrosation and nitration of amines and alcohols with nitrogen tetroxide, J. Amer. Chem. Sac., 79, 5832 (1957). (30) P. Gehlert and W. Rolle, Formation of diethylnitrosamine by reaction of diethylamine with nitrogen dioxide in the gas phase, Experientia, 33,579 (1977). (31) E. Boyland, The Effect of Some Ions of Physiological Interest on Nitrosamine Synthesis, in P. Bogovski, R. Preussman and E. A. Walker, "N-Nitroso Compounds: Analysis and Formation," IARC Scientific Publications no. 3, International Agency for Research on Cancer, Lyon, France, 1972, pp 124-126. (32) E. Boyland, E. Nice and K. Williams, The catalysis of nitrosation by thiocyanate from saliva, Food Cosmet. TaxicoL, 9, 639 (1971). (33) T. ¾. Fan and S. R. Tannenbaum, Factors influencing the rate of formation of nitrosomorpholine from morpholine and nitrite: acceleration by thiocyanate and other anions, J. Agr. Food Chem., 21,237 (1973). (34) S.S. Mirvish, J. Sams, T. ¾. Fan and S. R. Tannenbaum, Kinetics of nitrosation of the amino acids proline, hydroxyproline and sarcosine, J. Nat. Cancer Inst., 51, 1833 ( 1973). (35) F. Schweinsberg, Catalysis of Nitrosamine Synthesis, in P. Bogovski and E. A. Walker, "N-Nitroso Compounds in the Environment," IARC Scientific Publications no. 9, International Agency for Re- search on Cancer, Lyon, France, 1974, pp 80-85. (36) D. L. H. Williams, S-Nitrosation of thiourea and thiocyanate ion. Nitrosyl thiocyanate and the S-ni- troso-adduct of thiourea as nitrosating agents, J. Chem. Sac. Perkin Trans. 2,128 (1977). (37) E. Boyland and S. A. Walker, Thiocyanate Catalysis of Nitrosamine Formation and Some Dietary Im- plications, in P. Bogovski and E. A. Walker, "N-Nitroso Compounds in the Environment," IARC Scientific Publications no. 9, International Agency for Research on Cancer, Lyon, France, 1974, pp 132-136. (38) E. Kalatzis and J. H. Ridd, Nitrosation, diazotization and deamination. Part XII. The kinetics of N-ni- trosation ofN-methylaniline, J. Chem. Soc., B, 529 (1966). (39) S.S. Mirvish, Kinetics of nitrosamide formation from alkylureas, N-alkylurethans, and alkylgua- nidines. Possible implications for the etiology of human gastric cancer, J. Nat. Cancer Inst., 46, 1183 (1971). (40) S.S. Mirvish, Kinetics of N-Nitrosation Reactions in Relation to Tumorigenesis Experiments with Ni- trite Plus Amines or Ureas, in P. Bogovski, R. Preussmann and E. A. Walker, "N-Nitroso Com- pounds: Analysis and Formation," IARC Scientific Publications no. 3, International Agency for Re- search on Cancer, Lyon, France, 1972, pp 104-108. (41) R. C. Weast, "Handbook of Biochemistry, Selected Data for Molecular Biology," The Chemical Rub- ber Co., Cleveland, Ohio, 1968, p J131. (42) J. Tummavuori and P. Lumme, Protolysis of nitrous acid in aqueous sodium nitrate and sodium nitrite solutions at different temperatures, Acta Chem. Scand., 22, 2003 (1968). (43) J. D. Okun and M. C. Archer, Kinetics of nitrosamine formation in the presence of micelie-forming surfactants, J. Nat. Cancer Inst., 58,409 (1977). (44) J. D. Okun and M. C. Archer, Micellar Catalysis of Nitrosamine Formation, in E. A. Walker, P. Bogovski and L. Griciute, "Environmental N-Nitroso Compounds: Analysis and Formation," IARC
602 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Scientific Publications no. 14, International Agency for Research on Cancer, Lyon, France, 1976, pp 147-152. (45) M. C. Archer, H. S. Yang and J. D. Okun, Acceleration of Nitrosamine Formation at pH 3.5 by Microorganisms, in E. A. Walker, M. Castegnaro, L. Griciute and R. E. Lyle, "Environmental Aspects of N-Nitroso Compounds," IARC Scientific Publications no. 19, International Agency for Research on Cancer, Lyon, France, 1978, pp 239-246. (46) L. K. Keefer and P. P. Roller, N-Nitrosation by nitrite ion in neutral and basic medium, Science, 181, 1245 (1973). (47) P. P. Roller and L. K. Keefer, Catalysis of Nitrosation Reactions by Electrophilic Species, in P. Bogovski and E. A. Walker, "N-Nitroso Compounds in the Environment," IARC Scientific Publica- tions no. 9, International Agency for Research on Cancer, Lyon, France, 1974, pp 86-89. (48) M. C. Archer, S. R. Tannenbaum and J. S. Wishnok, Nitrosamine Formation in the Presence of Car- bonyl Compounds, in E. A. Walker, P. Bogovski and L. Griciute, "Environmental N-Nitroso Com- pounds: Analysis and Formation," IARC Scientific Publications no. 14, International Agency for Re- search on Cancer, Lyon, France, 1976, pp 141-146. (49) P. Gray and P. Rathbone, Dissociation of liquid dinitrogen tetroxide Henry's Law coefficients, heats and entropies of solution, and the thermodynamics of homolytic dissociation in the pure liquid, J. Chem. Soc., 3550 (1958) show the following influence of solvent on equilibrium constant K (moles/L) = [NO212/[N204] at 20øC. Solvent K x 10 5 Gas Phase 382 CC14 8.05 CHCIa 5.53 C6H6 2.23 (50) S.S. Mirvish, K. Karlowski, J.P. Sams and S. D. Arnold, Studies Related to Nitrosamide Formation: Nitrosation in Solvent: Water and Solvent Systems, Nitrosomethylurea Formation in the Rat Stomach and Analysis of a Fish Product for Ureas, in E. A. Walker, M. Castegnaro, L. Griciute and R. E. Lyle, "Environmental Aspects of N-Nitroso Compounds," IARC Scientific Publications no. 19, Interna- tional Agency for Research on Cancer, Lyon, France, 1978, pp 161-174. (51) R. M. Angeles, L. K. Keefer, P. P. Roller and S. J. Uhm, Chemical Models for Possible Artifactual Nitrosamine Formation in Environmental Analysis, in E. A. Walker, M. Castegnaro, L. Griciute and R. E. Lyle, "Environmental Aspects of N-Nitroso Compounds," IARC Scientific Publications no. 19, International Agency for Research on Cancer, Lyon, France, 1978, pp 109-115. (52) C.L. Bumgardner, K. S. McCallum and J.P. Freeman, Small ring heterocyclic nitrosamines, J. Amer. Chem. Soc., 83, 4417 (1961). (53) A.J. Buglass, B.C. Challis and M. R. Osborne, Transnitrosation and Decomposition of Nitrosamines, in P. Bogovski and E. A. Walker, "N-Nitroso Compounds in the Environment," IARC Scientific Publications no. 9, International Agency for Research on Cancer, Lyon, France, 1974, pp 94-100. (54) B.C. Challis and M. R. Osborne, The chemistry of nitroso compounds. Part VI. Direct and indirect transnitrosation reactions ofN-nitrosodiphenylamine, J. Chem. Soc. Perkin Trans. 2, 1526 (1973). (55) S, S. Singer, W. Lijinsky and G. M. Singer, Transnitrosation by aliphatic nitrosamines, Tetrahedron Lett., 1613 (1977). (56) S.S. Singer, W. Lijinsky and G. M. Singer, Transnitrosation: An Important Aspect of the Chemistry of Aliphatic Nitrosamines, in E. A. Walker, M. Castegnaro, L. Griciute and R. E. Lyle, "Environmental Aspects of N-Nitroso Compounds," IARC Scientific Publications no. 19, International Agency for Research on Cancer, Lyon, France, 1978, pp 175-181. (57) T. Y. Fan, R. Vita and D. H. Fine, C-Nitro compounds: a new class of nitrosating agents, Toxicol, Lett., 2, 5(1978). (58) A.M. Unrau, Reaction of 2-methyl-2-nitro-l,3-propanediol, Can. J. Chem., 42, 1741 (1964). (59) J. J. Warthesen, R. A. Scanlan, D. D. Bills and L. M. Libbey, Formation of heterocyclic N-nitrosamines from the reaction of nitrite and selected primary diamines and amino acids, J. Agric. FoodChem., 23,898 (1975). (60) S. Yanagida, D. J. Barsotti, G. W. Harrington and D. Swern, 2-Methyl-4-methoxy-l,2,3-oxadiaze- tidine. a correction, Tetrahedron Lett., 2671 (1973). (61) K. Eiter, K. F. Hebenbrok and H. J. Kabbe, Neue offenkettige und cyclische o•-Nitrosaminoalkyl- •ither, Justus Liebigs Ann. Chem., 765, 55 (1972).
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