2- -3-Chloro-butenoate

From a mechanistic point of view, the behaviour of the P-halogenated enoates is of interest (24). (Z)-3-Chloro-cinnamate and (Z)-3-chloro-butenoate as well as (Z)-3-bromo-cinnamate consume in the presence of enoate reductase 2 mol NADH per mol instead of 1 mol as other enoates do. The products are the saturated halogen-free carboxylates (Reaction [14]). 

Carbonylation of the complex 548 proceeds in ethanol gives ethyl 3-chloro-3-butenoate (554), The lactone 555 and the two esters 556 and 557 are obtained by carbonylation of the dimeric complex 549. The oxidative carbonylation of allene in ethanol with PdCl2 gives ethyl itacoante (558), although the yield is low[498]. 

In a further extension of this method, the enolate of the bislactim ether cyclo(L-Val-Gly) or cyclo(L-Val-Ala) were added to methyl (Z)-3-chloro-2-butenoate. The adduct is again a (Z)- ,/l-unsaturated ester and was obtained as a single diastereomer (d.r. > 99 l)207. For further examples see references cited ill the text. 

Acetic acid, vinyl- [3-Butenoic acid], 49 Acetone, ammo-, semicarbazone, hydrochloride [Hydrazinecarboxamide, 2-[l-(ammomethyl)ethyhdene], hydro chloride], correction note, 127 Acetone, chloro- [2 Propanone, 1-chloro ],... 

Kronberg L, Vartiainen T (1988) Ames mutagenicity and concentration of the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and of its geometric isomer E-2-chloro-3-(dichloromethyl)-4-oxo-butenoic acid in chlorine-treated tap waters. Mutat Res 206 177-182... 

The ozonolysis reaction, followed by reductive workup with sulfur dioxide, as described in Part A of the present procedure, illustrates a general method which has been developed for the preparation of acetals. Application of the procedure is illustrated by conversion of the following olefins in alcoholic solution to the corresponding acetals (1) l-chloro-4-(o-nitrophenyl)-2-butene to o-nitrophenylacetaldehyde dimethyl acetal in 84% yield (2) l,4-dibromo-2-butene tobromoacetaldehyde dimethyl acetal in 67% yield (3) 3-butenoic acid to malonaldehydic acid diethyl acetal ethyl ester in 61% yield (4) cyclopentadiene to malonaldehyde bis(diethyl acetal) in 48% yield and (5)... 

Four modes of degradation of 2 were discovered without the net consumption or production of redox equivalents. These four modes produce the final metabolites ethyl 3-ethoxy-4-chloro-2-butenoate, ethyl 3,3-bisethoxy-4-chlorobutanoate, oxol-2,4-dione, and 2,4-bischloromethyl-3,5-bisethoxycarbonyl-4-methyl pyridine. As a consequence, these modes do not depend on or disturb the glycolytic activity of the cell. 

If present, these modify the functional group(s), e.g., in 3-amino-2-chloro-2-butenoic acid, ethyl ester, hydrochloride. Modifications are used for anhydrides, esters, and salts of acids, oxides, sulfides, and selenides of ring systems containing P and As, hydrazones, and oximes of carbonyl compounds, salts of amines, etc. 

C4H5CI02 trans-2 chloro 2-butenoic acid 22038-56-8 40.00 1.1631 2 2895 C4H6N20 3-amino-5-methylisoxazole 1072-67-9 25.00 1.1256 2... 

C5H7CI02 methyl 4-chloro-2-butenoate 15320-72-6 420.65 36.315 2 4747 C5H8 3-methyl-1-butyne 598-23-2 302.15 26.020 1.2... 

C6H802 1,4-cyclohexanedione 637-88-7 444.11 38.541 2 7500 C6H9CI02 ethyl trans-2-chloro-2-butenoate 77825-53-7 450.15 39.116 1,2... 

C6H802 1-cyclopentene-1-carboxylic acid 1560-11-8 483.15 42.268 1,2 7501 C6H9CI02 ethyl cis-3-chloro-2-butenoate 6127-93-1 434.55 37.633 1,2 ... 

C6H802 ethyl 2-butynoate 4341-76-8 436.15 37.785 1.2 7502 C6H9CI02 ethyl trans-3-chloro-2-butenoate 6127-92-0 457.15 39.783 1,2... 

C6H802 parasorbic acid 10048-32-5 444.11 38.541 2 7510 C6H9CI03 methyl (E)-4-chloro-3-methoxy-2-butenoate 110104-60-1 430.82 37.279 2... 

C5H802 methyl cis-2-butenoate 4358-59-2 19.279 100.315 2 5046 C5H9CI 3-chloro-3-methyl-1-butene 2190-48-9 15.860 119.029 1.2... 

C5H802 methyl trans-2-butenoate 623-43-8 18.850 106.661 1.2 5047 C5H9CI 4-chloro-3-methyl-1 -butene 10524-01-3 16.700 116.199 1,2... 

C5H802 trans-2-methyl-2-butenoic acid 80-59-1 21.382 102.733 1,2 5051 C5H9CI 2-chloro-3-methyl-2-butene 17773-65-8 16.709 115.646 1,2... 

C5H802 cis-2-methyl-2-butenoic acid 565-63-9 21.460 101.430 1,2 5052 C5H9CI 3-chloro-2-ethyl-1-propene. .. 16.641 116.199 1,2... 

C5H802 2-methyl-3-butenoic acid 53774-20-2 21.668 100.344 2 5053 C5H9CI 1-chloro-2-methyl 1-butene 23378-11-2 16.988 114.720 1,2... 

C5H802 3-methyl-2-butenoic acid 541-47-9 21.107 103.841 1,2 5054 C5H9CI 1 -chloro-2-methyl-2-butene 13417-43-1 18.622 112.799 1,2... 

C5H802 3-methyl-3-butenoic acid 1617-31-8 21.696 100.343 2 5055 C5H9CI 1 -chloro-3-methyl-1 -butene 23010-00-6 15.995 115.572 2... 

Kronberg L., Christman R. F., Singh R., and Ball L. M. (1991) Identification of oxidized and reduced forms of the strong bacterial mutagen (Z)-2-chloro-3-(dichloromethyl)-4-oxo-butenoic acid (MX) in extracts of chlorine-treated water. Environ. Sci. Technol. 25, 99-104. 

An allyl halide, 3-chloro-2-methylpropene, was converted to 3-methyl-3-butenoic acid in 82% yield after 1 hr of reaction at room temperature. Wagner [65] converted 3-chloro-2-methylpropene to the Grignard in 81% yield after 10 hr at 14-16 C, and obtained 3-methyl-3-butenoic acid from the Grignard in 40% yield after CO2 quench. 

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