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Hydroperoxide anions reaction with borane

The synthetic value of the reaction lies in the modification of these organoboranes. The commonest reaction involves the decomposition of the borane by alkaline hydrogen peroxide. The highly nucleophilic hydroperoxide anion attacks the electron-deficient boron with the formation of an ate complex. Rearrangement of this leads to the formation of a borate ester which then undergoes hydrolysis to an alcohol in which an oxygen atom has replaced the boron (Scheme 3.15). The overall outcome of this reaction is the anti-Markownikoff hydration of the double bond. The regiochemistry is the reverse of the acid-catalysed hydration of an alkene. The overall addition of water takes place in a cis manner on the less-hindered face of the double bond. [Pg.71]

The reaction of alkenes with borane, monoalkyl and dialkylboranes leads to a new organoborane (see 15-16). Treatment of organoboranes with alkaline H2O2 oxidizes trialkylboranes to esters of boric acid." This reaction does not affect double or triple bonds, aldehydes, ketones, halides, or nitriles that may be present elsewhere in the molecule. There is no rearrangement of the R group itself, and this reaction is a step in the hydroboration method of converting alkenes to alcohols (15-16). The mechanism has been formulated as involving initial formation of an ate complex when the hydroperoxide anion attacks the electrophilic boron... [Pg.815]


See other pages where Hydroperoxide anions reaction with borane is mentioned: [Pg.162]    [Pg.464]    [Pg.1219]    [Pg.288]   
See also in sourсe #XX -- [ Pg.464 ]




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Borane anions

Borane reactions

Borane, with

Boranes anionic

Boranes hydroperoxides

Boranes reaction with

Boranes reaction with hydroperoxide anion

Boranes reactions

Hydroperoxidation reaction

Hydroperoxide anion

Hydroperoxide, reactions

Hydroperoxides reactions

Reaction with borane

Reaction with hydroperoxide anion

Reactions with anions

With boranes

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