Abstract
Methylcyclohexane dissolved in and forming a thin film on purified seawater with traces of anthraquinone added as triplet sensitizer was exposed to natural sunlight in a quartz flask. The water was circulated through a glass cartridge filled with Amberlite XAD-2 for the concentration of reaction products which were identified by GC/MS after elution and silica gel chromatography. They included isomeric methylcyclohexanols as the principal components, primary hydroperoxides, a tentatively identified secondary peroxide, methylcyclohexanones, and acyclic ketones. Mass spectra and mechanisms are discussed as well as possible biological consequences of the formation of these compounds.
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Kieber DJ, McDaniel J, Mopper K (1989) Nature 341:637–639
Mopper K, Stahovec WL (1986) Mar Chem 19:305–321
Kieber DJ, Mopper K (1987) Mar Chem 21(2):135–149
Kieber RJ, Zhou X, Mopper K (1990) Limnol Oceanogr 35:1503–1515
Mopper K, Zhou X, Kieber RJ, Kieber DJ, Sikorski RJ, Jones RD (1991) Nature 353:60–62
Harvey GR, Boran DA, Chesal LA, Tokar JM (1983) Mar Chem 12:119–132
Ehrhardt M (1987) Mar Chem 22:85–94
Ehrhardt MG, Burns KA (1990) J Exp Mar Biol Ecol 138:35–47
Ehrhardt MG, Burns KA, Bicego MC (1992) Mar Chem 37:53–64
Ehrhardt M, Petrick G (1993) Mar Chem 42:57–70
Blumer M, Thomas DW (1965) Science 148 No 3668:370–371
Blumer M, Guillard RRI, Chase T (1971) Mar Biol 8:183–189
Clark RC jr, Blumer M (1967) Limnol Oceanogr 12:79–87
Youngblood WW, Blumer M, Guillard RL, Fiore F (1971) Mar Biol 8:190–201
Scheuer PJ (1973) Chemistry of marine natural products. Academic Press, New York London, 199 pp
Rontani RF, Rambeloarisoa E, Bertrand JC, Giusti G (1985) Chemosphere 14:1909–1912
Ehrhardt M, Petrick G (1984) Mar Chem 15:47–58
Rontani JF, Bonin P, Giusti G (1987) Mar Chem 22:1–12
Ehrhardt M, Petrick G (1985) Mar Chem 16:227–238
Ehrhardt M, Weber RR (1991) Fresenius J Anal Chem 339:772–776
Petrov AA (1987) Petroleum hydrocarbons. Springer, Berlin Heidelberg New York, 255 pp
Trudgill PW (1984) Microbial degradation of alicyclic hydrocarbons. In: Watkinson RJ (ed) Developments in biodegradation of hydrocarbons—1. Applied Science Publishers, London, pp 47–84
Griffin WM, Cooney JJ (1979) Dev Ind Microbiol 20:479–488
Atlas RM (1981) Microbiol Rev 45:180–209
Gieskes WWC, Kraay GW (1982) Mar Biol 70:99–104
Laane RWPM, Gieskes WWC, Kraay GW, Eversdijk A (1985) Netherl J Sea Res 19:25–128
Momzikoff A, Santus R, Giraud M (1983) Mar Chem 12:1–14
Ehrhardt M, Bouchertall F, Hopf H-P (1982) Mar Chem 11:449–461
Fox MA, Olive S (1979) Science 205:582–583
Ehrhardt M (1987) ICES Techn Mar Environ Sci No 4:14 pp
Ehrhardt M, Derenbach J (1980) Mar Chem 8:339–346
Bolland JL, Cooper MR (1954) Proc Roy Soc 225A:405–426
Larson RA, Bott ThL, Hunt LL, Rogenmuser K (1979) Environ Sci Technol 13:965–969
Russel GA (1957) J Am Chem Soc 79:3871–3877
Zegota H, Schuchmann H-P, von Sonntag C (1984) J Phys Chem 88:5589–5593
Von Sonntag C, Schuchmann H-P (1991) Angew Chem 103:1255–1279
Madronich S, Calvert JG (1990) J Geophys Res 95(D5): 5697–5715
Schuchmann H-P, von Sonntag C (1984) Z Naturforsch 39B:217–221
Hellpointner E, Gäb S (1989) Nature 337:631–634
Heldal M, Norland S, Lien T, Knutsen G, Tjessem K, Aaberg A (1984) Environ Pollut 34:119–132
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Ehrhardt, M.G., Weber, R.R. Sensitized photo-oxidation of methylcyclohexane as a thin film on seawater by irradiation with natural sunlight. Fresenius J Anal Chem 352, 357–363 (1995). https://doi.org/10.1007/BF00322233
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DOI: https://doi.org/10.1007/BF00322233