Photoreduction of mirex in aliphatic amines

Alley, Earl G.; Layton, Blake; Minyard, J. P.

doi:10.1021/jf60194a044

Cited by 16 publications

(12 citation statements)

References 9 publications

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“…Carlson et al ( 8) observed environmental degradation of mirex in Mississippi soils treated 12 years previously and in mirex-containing bait lying in a small, shallow pond in Florida for 5 years. In all samples 8-monohydromirex was the predominant degradation product (10-20% of mirex levels), presumably resulting from photolysis (14,16). Lesser amounts (1-6% of mirex levels) of 10-monohydromirex, 2,8-dihydromirex, 5,10-dihydromirex, and kepone were found.…”

Section: Resultsmentioning

confidence: 84%

“…The main photoproduct is 8-monohydromirex as expected, with 10-monohydromirex and CioClnH (III) also being formed as minor products. The 10-monohydromirex may arise from photolysis of an amine-bound complex as found by Alley et al (15), or by photosensitized decomposition. Anaerobic bacterial degradation of mirex may account for some of the 10-monohydromirex formed in the Lake Ontario environment, but is a less likely source of 10monohydromirex than photolysis.…”

Section: Resultsmentioning

confidence: 90%

“…h Unknown compound, probable isomer of mirex. a mixture (14). CioClnH (III) was formed in small quantities from triphenylphosphine reduction of mirex (lower chromatogram, Figure 2) and is probably formed in small amounts in other mirex reductions which yield 8-monohydromirex.…”

Section: Resultsmentioning

confidence: 99%

“…The similarity of mass spectra and nearly identical retention time on packed columns of 8-monohydromirex and CioClnH (III) account for the lack of observation of the latter compound in other studies. The favored products of reductive dechlorination are either 8or 10-monohydromirex, depending on the mechanism of reduction (12)(13)(14)(15)(16)(17).…”

Section: Resultsmentioning

confidence: 99%

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Mirex and its degradation products in Great Lakes herring gulls

Norstrom¹,

Hallett²,

Onuska³

et al. 1980

Environ. Sci. Technol.

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Nitrated extracts of herring gull eggs from seven Lake Ontario colonies in 1977 were analyzed by glass capillary gas chromatography/mass spectrometry. Five minor mirex-related compounds were found in addition to mirex and the previously identified 8-monohydromirex (photomirex). The levels (milligrams/kilogram wet weight ± standard deviation) of all seven compounds were determined by high-resolution gas chromatography: 2,8-dihydromirex (0.016 ± 0.005); C10CI10H2 (II), possibly 3,8-dihydromirex (0.011 ± 0.003); 8monohydromirex (0.95 ± 0.14); CioClnH (III), possibly 9monohydromirex (0.077 ± 0.019); 10-monohydromirex (0.199 ± 0.025); mirex (2.58 ± 0.40); and C10CI12 (II) consistent with an isomer of mirex (0.039 ± 0.011). It was concluded that photodegradation was the only feasible mechanism for formation of these compounds, but that mirex and its photoproducts rapidly became sequestered in the ecosystem and protected from further degradation.

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Section: Resultsmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Mirex and its degradation products in Great Lakes herring gulls

Norstrom¹,

Hallett²,

Onuska³

et al. 1980

Environ. Sci. Technol.

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“…The structures of compounds 2, 3, and 5 were assigned from NMR, infrared, and mass spectral data. [2][3][4] The geometry of compound 4 was deduced in this study.…”

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confidence: 98%

Carbon-13 nuclear magnetic resonance spectra of chlorinated pentacyclo[5.3.0.02,6.03,9.04,8]decanes

Alley¹,

Layton²,

Minyard³

et al. 1976

J. Org. Chem.

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The resonances resulting from the various carbons in Kmethylglutarimide (6b) were assigned using off-resonance decoupling and by analogy with those in glutarimide6' (6c) and those reported for more highly substituted analogues by C. Dorlet and G. Van Binst, Anal. Lett., 6, 785 (1973). (64) Reference 19: CH3OC(=O)CH3 acld CH3 6 19.6, alcohol CH3 6 51.0 (neat). Reference 44: (CH&NCHO, ref 57; (CH&NCOCH3 amine CH3 ref 57, acid CH3 6 21.3 (dioxane). Reference 51: CH30C(=O)CH3 acid(65) Future plans include studying the I-hetera-3-cyclohexanone system in a manner similar to that used in this work. (66) CH3 6 20.4 [(CD3)2CO]; (CH&0)20 6 22.0 [(CD&CO]. (68) An electron diffraction study of gaseous 4-thiacyclohexanone (Ig) has recently provided evldence that the chair conformation is favored in this system: R. Seip, H. M. Seip, and 2. Smlth, to be published. (69) Values of 36.7 and 208.4 ppm have been obtained for l a in CDCI3 by another group: B. K. Carpenter, D. I. Rawson, and H. M. R. Hoffmann, Chern. Ind. (London), 866 (1975). (70) Similar conclusions are reached (based on unpublished results) in a recent review article: J. B. Lambert and s. I. Featherman, Chem. Rev., 75, 611 (1975).The 13C NMR spectra of dodecachloropentacyclo[5.3.0.02~6.03~9.04~8]decane and four of its hydrogen-substituted derivatives have been obtained. The assignment of the 13C resonances was based on chemical shifts, coupling constants, and Overhauser enhancements of the signals. Good correlation was found between the observed chemical shifts and those predicted from substituent parameters and between lH chemical shifts and 13C chemical shifts. Some unusual variations in the two-and three-bond coupling constants were observed.

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Studies on the dechlorination and detoxification of organochlorine compounds II. Chlorinated cyclodiene insecticides and the polychlorinated insecticide ‘mirex’

Stojkovski

Markovec

Magee

1991

J of Chemical Tech & Biotech

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In the first paper on the dechlorination of organochlorine compounds, results were reported for polychlorinated biphenyls and polychlorinated naphthalenes, using the Ni2B in‐situ catalytic dechlorination technique. In the present study, the work has been extended to the dechlorination and detoxification of some chlorinated polycyclic hydrocarbons belonging to a cyclodiene insecticide group (dieldrin, aldrin and endrin). In addition, a cage‐structured polychlorinated insecticide, ‘mirex’, has also been investigated. During the dechlorination process, intermediates were detected by GC/MS and identified by their characteristic mass fragments and retention in mass.

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Photoreduction of mirex in aliphatic amines

Cited by 16 publications

References 9 publications

Mirex and its degradation products in Great Lakes herring gulls

Mirex and its degradation products in Great Lakes herring gulls

Carbon-13 nuclear magnetic resonance spectra of chlorinated pentacyclo[5.3.0.02,6.03,9.04,8]decanes

Studies on the dechlorination and detoxification of organochlorine compounds II. Chlorinated cyclodiene insecticides and the polychlorinated insecticide ‘mirex’

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