2.2- dimethyl-cyclopropane carboxylic acid

Compounds that affect Host Reactions. Examples of compounds which enhance or induce host reactions to pathogens include 2,2-dichloro-3,3-dimethyl-cyclopropane carboxylic acid (DDCC), probenazole, and fosetyl-Al (4). Although these chemicals do not stop the fungus from penetrating the plant, they are quite effective at preventing colonization through the enhancement of the host s resistance mechanisms. Further studies are needed to elucidate how these resistance mechanisms are triggered. 

The first example of asymmetric organometallic catalysis outside the area of polymer chemistry was the cyclopropanation of alkenes as described by Nozaki, Noyori et al. in 1966 [17]. The chiral catalyst used was a salen-copper complex 3 (Scheme 3), giving a maximum enantioselectivity of 10% ee. These low but well-established values initiated further research in this area. Later, Aratani et al. initiated the tuning of the structure of the copper catalyst at Sumitomo [18]. They were able to reach quite high level of enantioselectivity with copper catalyst 4. For example, 2,2-dimethyl-cyclopropane carboxylic acid was obtained in 92% ee, and subsequently used in a process to prepare cilastatine. 

Permethrinic acid has two enantiomer pairs and four isomers (2" = 4) (Table B33, Appendix B). The acid leaving group for permethrin, cypermethrin, and cyfluthrin is permethrinic acid. The structure of this acid is given in Table 3. Angerer and Ritter (1997) separated the methyl esters of cis- and trans-permethrinic acid on a polysiloxane capillary column by GC (Table C18, Appendix C). The carboxylic acids of several of these pyrethroids were also listed as trans- or cw-3-(2, 2-dichlorovinyl)-2, 2-dimethyl cyclopropane carboxylic acid. The acids may be separated on a CHIREX phase 3005 column (Phenomenex, 2320 W 205th Street, Torrance, CA 90501) by HPLC. 

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... 

R and R may be H, methyl, cyclopropyl, cyano, or ester groups. The phenylcarbene formed on irradiation of trans-l,2-diphenyloxirane has been trapped and identified in the form of a cyclopropane derivative in methanol in the presence of benzyl methyl ether and alkenes. Photolysis in the presence of 2,3-dimethyl-2-butene proceeds by cycloaddition with the formation of cyclopropane-carboxylic acid and oxetane derivatives (Eq. 368). ... 

More investigations have been performed with cyclopropyl ketones. The isomerization of the cis-cyclopropyl ketone 209 to its trans isomer 210 was only achieved by means of the rather basic dimsyl sodium in dimethyl sulfoxide at 60°C . Similarly, esters of cyclopropane carboxylic acids have been isomerized ... 

AI3-29062 Anchimanaito 20S Anvil Anvil 2 2 ULV Anvil 10 10 ULV Benzyl alcohol, m-phenoxy-, 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanxxboxylate Caswell No. 652B CCRIS 2602 Cyclopropanecarboxylic xid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(phenoxy-phenyl)methyl ester, cis,trans-( )- Cyclopropane-carboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,... 

Synonyms Cyclopropane carboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, (2-methyl (1,r-biphenyl)-3-yl) methyl ester, (z)-... 

CAS 28434-01-7 EINECS/ELINCS 209-542-4 Synonyms (5-Benzyl-3-furyl) methyl(1 R)-trans-chrysanthemate 1 R-trans-2,2-Dimethyl-3-(2-methylpropenyl) cyclopropane carboxylic acid (5-benzyl-3-furyl) methyl ester (5-(Phenylmethyl)-3-furanyl) methyl-1 R-trans-2,2-dimethyl-3-(2-methylpropenyl)... 

Cyclopropane carboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, (5-benzyl-3-furyl) methyl ester. See Resmethrin... 

R -h )-tr s-Chrysanthemic acid 2,2-Dimethyl-3-(2-methylpropenyl)cyclopropane-carboxylic acid... 

Hydrolysis of the pyrethroids may occur prior to hydroxylation. For dichloro groups (i.e., cyfluthrin, cypermethrin and permethrin) on the isobutenyl group, hydrolysis of the trans-isomers is the major route, and is followed by hydroxylation of one of the gem-dimethyls, the aromatic rings, and hydrolysis of the hydroxylated esters. The cis-isomers are not as readily hydrolyzed as the tran -isomers and are metabolized mainly by hydroxylation. Metabolism of the dibromo derivative of cypermethrin, deltamethrin, is similar to other pyrethroids (i.e., cyfluthrin, cypermethrin, and permethrin) that possess the dichloro group. Type 11 pyrethroid compounds containing cyano groups (i.e., cyfluthrin, cypermethrin, deltamethrin, fenvalerate, fenpropathrin, and fluvalinate) yield cyanohydrins (benzeneacetonitrile, a-hydroxy-3-phenoxy-) upon hydrolysis, which decompose to an aldehyde, SCN ion, and 2-iminothia-zolidine-4-carboxylic acid (TTCA). Chrysanthemic acid or derivatives were not used in the synthesis of fenvalerate and fluvalinate. The acids (i.e., benzeneacetic acid, 4-chloro-a-(l-methylethyl) and DL-valine, Af-[2-chloro-4-(trifluoromethyl) phenyl]-) were liberated from their esters and further oxidized/conjugated prior to elimination. Fenpropathrin is the oifly pyrethroid that contains 2,2,3,3-tetramethyl cyclopropane-carboxylic acid. The gem-dimethyl is hydroxylated prior to or after hydrolysis of the ester and is oxidized further to a carboxylic acid prior to elimination. 

Cyclopropane carboxylic acid, 2, 2-dimethyl-3-(2-methyl-l-propenyl)-, (1,3,4,5,6,7-hexahydro-l,3-dioxo-2 H-isoindol-2-yl)methyl ester... 

Ethyl chrysanthemate (ethyl 2,2-dimethyl-3 c and t -[2-methylpropenyl]-cyclopropane carboxylate) [97-41-6] M 196.3, b 98-102 /llmm, 117-121 /20mm. Purified by vacuum distn. The free trans-acid has m 54° (from, EtOAc) and the free cis-acid has m 113-116° (from EtOAc). The 4-nitrophenyl ester has m 44-45° (from pet ether) [Campbell and Harper J Chem Soc 283 1945 IR Allen et al. JOrg Chem 21 29 1957]. 

Allyldiethylamine behaves similarly, but the yields are low since neither the starting amine nor the products are stable to the reaction conditions. For the efficiency of the cyclopropanation of the allylic systems under discussion, a comparison can be made between the triplet-sensitized photochemical reaction and the process carried out in the presence of copper or rhodium catalysts whereas with allyl halides and allyl ethers, the transition metal catalyzed reaction often produces higher yields (especially if tetraacetatodirhodium is used), the photochemical variant is the method of choice for allyl sulfides. The catalysts react with allyl sulfides (and with allyl selenides and allylamines, for that matter) exclusively via the ylide pathway (see Section 1.2.1.2.4.2.6.3.3. and Houben-Weyl, Vol. E19b, pll30). It should also be noted that the purely thermal decomposition of dimethyl diazomalonate in allyl sulfides produces no cyclopropane, but only the ylide-derived product in high yield.Very few cyclopropanes have been synthesized by photolysis of other diazocarbonyl compounds than a-diazo esters and a-diazo ketones, although this should not be impossible in several cases (e.g. a-diazo aldehydes, a-diazocarboxamides). Irradiation of a-diazo-a-(4-nitrophenyl)acetic acid in a mixture of 2-methylbut-2-ene and methanol gave mainly l-(4-nitrophenyl)-2,2,3-trimethylcyclo-propane-1-carboxylic acid (19, 71%) in addition to some O-H insertion product (10%). ... 

Hydrolysis of ( —)-methyl (15,3S)-(2,2-dimethyl-3-tosyloxycyclobutyl)acetate, obtained by a stereocontrolled route from (-f )-a-pinene, with zinc(II) acetate in aqueous dimethoxyethane at 80 °C leads to optically active 5-lactone ( —)-(lS,65)-2,2-dimethyl-3-oxabicyclo[4.1.0]heptan-4-one (1) in 62% yield.In addition to this cyclopropane derivative, a carboxylic acid was isolated which on treatment with diazomethane gave (-f )-methyl (5,5-dimethyl-2-tetrahydrofuryl)acetate (2). 

Reductive carbonylation of 1,1-dibromocyclopropanes with tetracarbonylnickel in dimethyl-formamide in the presence of a nucleophile is a powerful method for direct introduction of carboxylic acid functions to cyclopropanes. Nucleophiles, such as alcohols, amines, and silylamines, are particularly reactive and give cyclopropyl esters and amides, respectively, in reasonable to good yields, e.g. formation of 5 and... 

Indoline-2-carboxylic acid /9S767-06-7/M 163.2, m 177"(dec), [a] +11.0" (c 0.3, MeOH)- Purify it as for the S-enantiomer below. The R-(+)-hydrochloride has [172152-19-1]. It is a proline based oiganocatalyst which promotes the enantioseleetive formation of cyclopropanes by reaction between 2-(dimethyl-X -sulfanylidene)-l-phenyl-ethanone (for stable sulfonium ylides see Ratts Yao J Org Chem 31 1185 1966) and but-2-enals in high yields and very high stereoselectivity involving Direct Electrostatic Activation (DEA) [Kunz Mac Millan JA/w Chem Soc 127 3240 2005.]... 

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