Cyclopropane carboxylic acids

Amino-5-chlorobenzophenone Cyclopropane carboxylic acid chloride Phthalimidoacetyl chloride... 

Preparation of 2-Cyclopropylcarbony/amido-5-Chlorobenzophenone To 400.5 g (1.73 mols) of 2-amino-5-chlorobenzophenone dissolved in 220 g (2.18 mols) of triethylamine and 3.5 liters of tetrahydrofuran is added cautiously 181 g (1.73 mols) of cyclopropane-carboxylic acid chloride. The reaction is refluxed 2 /2 hours and allowed to cool to room temperature. The solvent is then removed under vacuum to obtain 2-cyclopropylcarbonyl-amido-5-chlorobenzophenone as a residue which is dissolved in 1 liter of methylene chloride, washed twice with 5% hydrochloric acid, and then twice with 10% potassium hydroxide. The methylene chloride solution is then dried over anhydrous magnesium sulfate, filtered and the solvent removed under vacuum. The residue is recrystallized from 1,500 ml of methanol, charcoal-treating the hot solution to give 356 g of 2-cyclopropylcarbonylamido-5-chlorobenzophenone, MP 105° to 105.5°C (69% yield). 

Cyclopropane carboxylic acid is degraded via 3-hydroxybutyrate by both the bacterium Rhodococcus rhodochrous (Toraya et al. 2004) (Figure 7.33) and by fungi (Schiller and Chung 1970), although the mechanism for ring fission has not been determined. 

Optical resolution methods with carane-3,4-diol are noteworthy for wide generality. Esters of various cyclopropane carboxylic acids with (1,S, 3A>,4A>,6A>)-carane-3,4-diol were prepared and all (lR)-isomers could easily be obtained by a simple silica gel column chromatography. 

The specific feature of the bonds also affects its chemical behaviour and the stereochemistry of substitution reactions. For example in the conversion of (-) trans -2, 3 diphenyl cyclopropane carboxylic acid into (+) 1, 3 diphenylallene the optical activity is retained. 

The synthesis of compounds 39, 41, and 43 by the ODPM rearrangement opens a novel photochemical route to chrysanthemic acid and other cyclopropane carboxylic acids present in pyrethrins and pyrethroids [52]. In fact, aldehyde 43 can be transformed to tran -chrysanthemic acid by simple oxidation. This new synthetic route to ecologically benign insecticides competes with the one previously described by us using the 1-ADPM rearrangement of p,y-unsaturated oxime acetates [30,53]. 

Finally, an entirely different approach to milnacipran (2) was recently reported in the literature (Scheme 14.6). In this case, the general strategy is based on position-selective deprotonation of cyclopropane carboxamides. Thus, cyclopropane amide 27, which was easily prepared from commercially available cyclopropane carboxylic acid, underwent... 

Ethyl a-lithiocyclopropanecarboxylate (1) could not be alkylated only the self-addition product 2 was isolated60,61. The dilithiated cyclopropane carboxylic acid 4, however, reacted with low conversion to give the a-alkylated products 562. 

The checkers obtained cyclopropylcarbinol from the Aldrich Chemical Company, Inc. It can be readily prepared by the reduction of cyclopropane-carboxylic acid with lithium aluminum hydride. ... 

L-CCG 1, selective group II mGluR agonist, 2-(Amino-carboxy-methyl)-cyclopropane-carboxylic acid... 

Nanda S, Rao AB et al (1999) Enzyme catalysed kinetic resolution of racemic 2,2-dimethyl-3-(2,2-disubstituted vinyl) cyclopropane carboxylic acids anchored on polymer supports. Tetrahedron Lett 40 5905-5908... 

C4H602)t Ci s-crotonic, trans-crotonic 3-butenoic, methacrylic and cyclopropane carboxylic acids 210 g, n 425... 

C6H402)t Cis-crotonic, traus-crotonic methacrylic, 3-butenoic and cyclopropane carboxylic acids 100-110 g. n, p 425... 

Cyclopropane carboxylic acid chloride cyprofuram, profluralin, trinexapac Cyclopropylamine cyprazine, cyromazine, procyazine Cyclopropyl p.chloro phenyl ketone flucycloxuron... 

Cyclopropane carboxylic acid (1) Cyclopropane bromide + KCN - cyclopropane cyanide followed by hydrolysis (2) Ethylene dibromide + diethyl malonate - cyclopropane dicarboxylic acid followed by saponification and monodecarboxylation via heating... 

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