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Timestamp: 2019-04-20 12:34:03+00:00

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Physical Data: mp 30-35 °C; bp 75 °C/0.1 mmHg.
Solubility: sol dichloromethane, carbon disulfide, carbon tetrachloride.
Form Supplied in: white solid or liquid, 7.8 M in BHBr2.
Handling, Storage, and Precautions: corrosive liquid; air and moisture sensitive; flammable; stench. Handle and store under nitrogen or argon. Stable indefinitely when stored under nitrogen at 25 °C. Reacts violently with water. This reagent should be handled in a fume hood.
Selective Hydroboration of Dienes and Enynes.
Reactions of Alkenyldibromoboranes and Alkenylalkylbromoboranes.
Synthesis of Alkenylboronic Acids, Alkenes, Aldehydes, and Ketones.
Alkenyldibromoboranes undergo many of the characteristic reactions of alkenylboranes. The presence of dimethyl sulfide does not interfere in their transformations. Protonolysis with acetic acid in refluxing dichloromethane gives the corresponding alkene. Oxidation leads to aldehydes or ketones (eq 4).3 Hydrolysis and alcoholysis yields alkenylboronic acids and esters, respectively.
Synthesis of (E)- and (Z)-Alkenes, Trisubstituted Alkenes, 1,2-Disubstituted Alkenyl Bromides, Ketones, and Enolborates.
The synthesis of (Z)-alkenes, according to eq 4, is a simple, convenient method, provided the alkynic precursor is readily available. A general Zweifel (E)- and (Z)-alkene synthesis starts with 1-alkynes and 1-bromo-1-alkynes, respectively. The precursors are hydroborated with monoalkylbromoborane to give the corresponding alkylalkenylbromoboranes. Migration of the alkyl group completes the formation of the carbon skeleton (eq 6).19-21 The procedure allows full utilization of the alkyl group.
Synthesis of (E)- and (Z)-1-Halo-1-alkenes and a-Bromoacetals.
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