Meso-2,3-Dibromosuccinic acid

This is supported by the fact that the reaction with fumaric acid gives meso-dibromosuccinic acid, whereas maleic acid gives the chiral dibromosuccinic acid, of course as a racemic mixture. Note that these reactions are stereospecific. 

G) Addition to a trans olefin usually gives a meso product. Addition to a cis olefin leads to a racemic modification. Thus when bromine is added to maleic acid, racemic dibromosuccinic acid is formed. When the same reaction is carried out with fumaric acid, the product is mostly meso-dibromosuccinic acid.10... 

The reactivity of these isomers in electrode reactions has been investigated in a number of papers [22, 27, 83-87]. Elving and co-workers [22, 77] investigated the polarographic behavior of racemic and meso-dibromosuccinic acids and their diethyl esters and found that the half-wave potentials of the diastereoisomers were somewhat different. 

These terms are best illustrated by examples. Thus, if maleic acid treated with bromine gives the dl pair of 2,3-dibromosuccinic acid while fumaric acid gives the meso isomer (this is the case), the reaction is stereospecific as well as stereoselective because two opposite isomers give two opposite isomers ... 

CjHjBrjN 626-05-1) see Acrivastine meso-2,3-dibromosuccinic acid (C4H4Br204 608-36-6) see Biotin... 

Maleic acid when treated with bromine gives dl pair of 2, 3 dibromosuccinic acid while fumaric acid gives the meso isomer. 

Any reaction in which only one of a set of stereoisomers is formed exclusively or predominantly is called a stereoselective synthesis.184 The same term is used when a mixture of two or more stereoisomers is exclusively or predominantly formed at the expense of other stereoisomers. In a stereospecific reaction, a given isomer leads to one product while another stereoisomer leads to the opposite product. All stereospecific reactions are necessarily stereoselective, but the converse is not true. These terms are best illustrated by examples. Thus, if maleic acid treated with bromine gives the dl pair of 2,3-dibromosuccinic acid while fumaric acid gives the meso isomer (this is the case), the reaction is stereospecific as well as stereoselective because two opposite isomers give two opposite isomers ... 

There is much evidence that when the attack is by Br+ (or a carrier of it), the bromonium ion 2 is often an intermediate and the addition is anti. As long ago as 1911, McKenzie and Fischer independently showed that treatment of maleic acid with bromine gave the dl pair of 2,3-dibromosuccinic acid, while fumaric acid (the trans isomer) gave the meso compound.5 Many similar experiments have been performed since with similar results. For triple bonds, stereoselective anti addition was shown even earlier. Bromination of dicarboxyacetylene gave 70% of the trans isomer.6... 

C3H10CiN trimethylamine hydrochloride 593-81-7 25.00 0,9092 2 2521 C4H4Br204 meso-2,3-dibromosuccinic acid 526-78-3 25.00 2.1862 2... 

R RgCX—R3R4CX, the products of the initial two-electron electrode reaction are the halide ions and a more unsaturated species, RjR2C=CRgR4. The dualistic nature of the reaction can be illustrated in terms of the reduction of the meso, a, a -dibromo-succinic acid which forms only fumaric acid over the normal pH range and of the racemic a, a -dibromosuccinic acid which also forms maleic acid in varying amount in the intermediate pH range associated with the presence of the mono anion. ... 

Halogen-Substituted Compounds. Elving and co-workers [22, 83] investigated the reduction of meso- and racemic dibromo-succinic acids at a mercury cathode. At all pH values the meso acid gave only fumaric acid, i,e., trans-elimination of bromine occurred. Racemic dibromosuccinic acid gives various products depending on the pH fumaric acid alone is also formed in strongly acidic and alkaline solutions, i.e., cis-elimination of bromine occurs, but at pH values between 0.4 and 6.9 a mixture of fumaric acid and maleic acid is formed, and the latter is the main product at pH 4 (70% yield). 

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