8-Bromo octene

Like 6-chloro-1-hexene, 8-chloro-1-octene contains a small amount (3-5%) of the corresponding bromide (8-bromo-1-octene), which is not a problem in some reactions. 

Bromo octene-1 2,2-Dimethyl-7-bromo-heptanoic acid 2-Methyl-2-ethyl-6-bromo-hexanoic acid ... 

Reaction of 4-octyne with trifiuoroacetic acid in CH2CI2 containing 0.1-1.0A/Br leads mainly to Z-4-bromo-4-octene by an anti addition. The presence of Br greatly accelerates the reaction as compared to reaction with trifiuoroacetic acid alone, indicating the involvement of the Br in the rate-determining step. ... 

In addition to its effect on stability, delocalization of the unpaired electron in the allyl radical has other chemical consequences. Because the unpaired electron is delocalized over both ends of the nr orbital system, reaction with Br2 can occur at either end. As a result, allylic bromination of an unsymmetrical alkene often leads to a mixture of products. For example, bromination of 1-octene gives a mixture of 3-bromo-l-octene and l-bromo-2-octene. The two products are not formed in equal amounts, however, because the intermediate allylic radical is... 

The results of the olefin oxidation catalyzed by 19, 57, and 59-62 are summarized in Tables VI-VIII. Table VI shows that linear terminal olefins are selectively oxidized to 2-ketones, whereas cyclic olefins (cyclohexene and norbomene) are selectively oxidized to epoxides. Cyclopentene shows exceptional behavior, it is oxidized exclusively to cyclopentanone without any production of epoxypentane. This exception would be brought about by the more restrained and planar pen-tene ring, compared with other larger cyclic nonplanar olefins in Table VI, but the exact reason is not yet known. Linear inner olefin, 2-octene, is oxidized to both 2- and 3-octanones. 2-Methyl-2-butene is oxidized to 3-methyl-2-butanone, while ethyl vinyl ether is oxidized to acetaldehyde and ethyl alcohol. These products were identified by NMR, but could not be quantitatively determined because of the existence of overlapping small peaks in the GC chart. The last reaction corresponds to oxidative hydrolysis of ethyl vinyl ether. Those olefins having bulky (a-methylstyrene, j8-methylstyrene, and allylbenzene) or electon-withdrawing substituents (1-bromo-l-propene, 1-chloro-l-pro-pene, fumalonitrile, acrylonitrile, and methylacrylate) are not oxidized. 

Octene 1-Bromo-pcntadecafluoro-E10b, 471 (Educt) E10b2. 135 ( TF -> En)... 

Exercise 11-12 a. Draw the structure and configuration of the product expected of the reaction between 1-bromo-1-hexyne and diethylborane, (C2H5)2BH. b. When the product is treated with sodium methoxide, NaOCH3, then with propanoic acid, frans-3-octene is formed, Show the steps involved in forming this frans-alkene. 

Okano and coworkers accomplished ATRA of very deactivated (l-bromo-2,2,2-trifluoroethyl)benzenes 224 with 1-octene 223 in the presence of 10 mol% CuCI and 20 mol% bipy 26 and obtained 18-81% of the atom transfer addition products 225 as a 2 1 syn/anti mixture (Fig. 56) [293],... 

Aliphatic olefins and (z-btoraocarboxylic esters yield y-bromo esters in good yields, as illustrated by the formation of ethyl y-bromocapoate from 1-octene and ethyl bromoacetate (57%). ... 

Elimination of bromine and ethoxyl groups with zinc is much the same as the elimination of two adjacent halogen atoms. The /6-bromo ether is heated with a stirred suspension of powdered zinc or zinc-copper couple in 90-95% ethanol, n-propyl alcohol, or isopropyl alcohol. The preparation of 3 Octene fails in n-propyl alcohol. In several cases the products have been shown to be mixtures of cis and trans isomers. The yields for the first two steps of the synthesis are 70-90%. The coupling of the a,/S-dibromo ethers with primary Grignard reagents takes place in 50-80% yields, whereas with secondary Grignard reagents only 30-55% yields are obtained. 

As a result of an extensive study, it has been found that methylene groups are attacked much more readily than a methyl group. For example, 2-methyl-2-butene requires 16 hours for completion of the reaction, whereas, 2-methyl-2-hexene requites 10 minutes. The conversion of cyclohexene to 3-broraocyclohexene is accomplished in 20 minutes in 87% yield. It is noteworthy that the bromination of 1-octene with N-btomo-succinimide yields a mixture of l-bromo-2-octene and 3-bromo-1-octene and that the proportion of these isomers is in close agreement with the equilibrium mixture formed at 100° by analogous bromides. ... 

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