| 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
|
| Holdings |
| Library |
Call Number |
Additional Info |
Location |
Last
Modified |
Checkout
Status |
| NTIS |
PB-274 739 |
Some EPA libraries have a fiche copy filed under the call number shown. |
|
07/26/2022 |
|
| Collation |
11p |
| Abstract |
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. |
| Supplementary Notes |
Pub. in Canadian Jnl. of Chemistry, v49 n23 1971. Prepared in cooperation with Environmental Protection Agency, Chamblee, Ga. Chamblee Toxicology Lab.; National Research Council of Canada, Ottawa (Ontario). |
| Availability Notes |
Included in the report, Journal Articles on Pesticide Chemistry, PB-274 732. |
| Title Annotations |
Reprint: On the Chemistry of the Isomeric Dichlorodiphenylacetaldehydes Related to DDT. Stereoelectronic Effects in the Hydrolysis of their Cyclic Acetals, |
| PUB Date Free Form |
7 Jul 70 |
| Category Codes |
7C; 6F; 99D; 57P |
| NTIS Prices |
(Order as PB-274 732, MF A01) |
| Primary Description |
500/01 |
| Document Type |
NT |
| Cataloging Source |
NTIS/MT |
| Control Number |
323728472 |
| Origin |
NTIS |
| Type |
CAT |
