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Parlar, H.A. ; Mansour, M. ; Baumann, R.

Photoreactions of hydroxychlordene in solution, as solids, and on the surface of leaves.

J. Agric. Food Chem. 26, 1321-1324 (1978)

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Open Access Green as soon as Postprint is submitted to ZB.

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The photoreactions of the heptachlor transformation product 1-exo-hydroxychlordene (exo-4,5,6,7,-8,8-hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoinden-1-ol) (2) dissolved in organic solvents, as a solid on glass, and dispersed on plant leaf surfaces have been investigated. In addition to the (2 + 2) cycloaddition typical for this substance class, an entirely novel intramolecular photoisomerization reaction was found. This reaction leads to cyclic ketone, 1,1a,2,2,3,exo-6-hexachloro-1a,2,3,3a,5a,5b-hexahydro-1,3-methano-1H- cyclobuta[cd]pentalen-4-one (8), whose structure was established by spectral data obtained by mass spectrometry, infrared spectrometry, and 1H and 13C nuclear magnetic resonance measurements.

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