67401-40-5Relevant academic research and scientific papers
Nitrile biotransformation for highly enantioselective synthesis of 3-substituted 2,2-dimethylcyclopropanecarboxylic acids and amides
Wang, Mei-Xiang,Feng, Guo-Qiang
, p. 621 - 624 (2003)
Biotransformations of differently configured 2,2-dimethyl-3-substitued-cyclopropanecarbonitriles were studied using a nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 whole-cell catalyst under very mild conditions. Although all of the cis-3-aryl-2,2-dimethylcyclopropanecarbonitriles appeared inert toward the biocatalyst, a number of racemic trans-isomers efficiently underwent a highly enantioselective hydrolysis to produce (+)-(1R,3R)-3-aryl-2,2-dimethylcyclopropanecarboxylic acids and (-)-(1S,3S)-3-aryl-2,2-dimethylcyclopropanecarboxamides in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of 1R-enantioselective nitrile hydratase and amidase, with the later being a dominant factor. The influence of the substrates on both reaction efficiency and enantioselectivity was discussed in terms of steric and electronic effects. Coupled with chemical transformations, biotransformations of nitriles provided convenient syntheses of optically pure geminally dimethyl-substituted cyclopropanecarboxylic acids and amides, including chrysanthemic acids, in both enantiomeric forms.
Search for Routes of Synthesis of Permethrin and Chloropermethrin Starting from Halogen-containing Alkenoic Acids
Badanyan,Stepanyan,Mikaelyan,Ovivyan,Panosyan
, p. 34 - 41 (2007/10/03)
Promising procedures were developed for the synthesis of permethrin and I-chloropermethrin starting from acid chloride, nitrile, and esters of 3,3-dimethyl-2,2,4,6,6-pentachloro-5-alkenoic acid and 3,3-dimethyl-2,2,6,6-tetrachloro-5-alken-4-olide, which were prepared by adding derivatives of trichloroacetic acid to 1,1-dichloro-4-methyl-1,3-pentadiene in the presence of catalytic amounts of monovalent copper ions and amine.
Synthesis of ethyl (+/-)-cis-3-(2,2-dihalogenovinyl)-2,2-dimethylcyclopropanecarboxylate
Genet, J. P.,Denis, A.,Charbonnier, F.
, p. 793 - 796 (2007/10/02)
The two (+/-) cis pyrethroid ethyl esters 2a,b have been synthesized.These esters are obtained via stereoselective ScN' cyclization of 3b to 5b.Desulfonylation of 5b with retention of configuration at low temperature (Na/Hg, -30 deg C) affords (+/-)-cis-chrysanthemonitrile 6.This nitrile is converted into cis aldehyde 7 which by Wittig reaction provides pyrethroid nitriles 8a and 8b, respectively.Finally hydrolysis of the nitrile group gives the esters 2a and 2b in 30percent overall yield from 3b.
