Record Display for the EPA National Library Catalog


OLS Field Name OLS Field Data
Main Title On the Chemistry of the Isomeric Dichlorodiphenylacetaldehydes Related to DDT. Stereoelectronic Effects in the Hydrolysis of their Cyclic Acetals.
Author McKinney, J. D. ; Hawk, R. E. ; Boozer, E. L. ; Suggs., J. E. ;
CORP Author National Inst. of Environmental Health Sciences, Research Triangle Park, N.C. ;Environmental Protection Agency, Chamblee, Ga. Chamblee Toxicology Lab. ;National Research Council of Canada, Ottawa (Ontario).
Year Published 1970
Stock Number PB-274 739
Additional Subjects Pesticides ; Synthesis(Chemistry) ; Chlorine organic compounds ; Hydrolysis ; Chemical reactions ; Metabolism ; Reprints ; Acetaldehyde/dichloro-diphenyl
Library Call Number Additional Info Location Last
NTIS  PB-274 739 Most EPA libraries have a fiche copy filed under the call number shown. Check with individual libraries about paper copy. 06/23/1988
Collation 11p
The chemistry of the isomeric dichlorodiphenylacetaldehydes related to DDT was investigated to aid in delineating their possible role in the metabolism of this pesticide. In the case of the p,p'-isomer, the most important system under consideration, several literature syntheses were shown to be incorrect. The failure of at least one of these methods was attributed to the preferred oxidative involvement of the benzhydryl carbon via rearrangement of a beta-hydroxy enol ether which normally led to the isolation of the p,p'-dichlorobenzophenone instead of the desired aldehyde. The o,p'-isomer exhibited chemistry similar to that of the p,p'-isomer although the steric effect of the ortho-substituted chlorine on the benzhydryl proton was notable. The o,o'-isomer was normal in that it did not undergo reactions involving the benzhydryl carbon. Some possible mechanistic and biological implications of the work are discussed.