Alkylboranes, oxidation synthesis

DIMETHYL-3-PHENYLPRO-PIONALDEHYDE, 54, 46 Alkylboranes, oxidation, 52, 59 synthesis, 52, 59 Alkyl bromides, from alcohols, 54, 66... 

The second reaction (Equation 11 -3) achieves the synthesis of a primary alcohol by the oxidation of the alkylborane with hydrogen peroxide in basic solution. Starting with a 1-alkene, one can prepare a primary alcohol in two steps ... 

Although water, in some cases, has undergone addition across the C-C double bond in a vinylcyclopropane under acidic, - neutral, " and basic " - aqueous conditions, e.g. formation of 2, the reaction has more often been performed using a two-step procedure. Most frequently used was a one-pot synthesis consisting of hydroboration followed by oxidation with hydrogen peroxide/sodium hydroxide. The alkylboranes, formed in the first step, can be isolated. - The first step has generally been carried out using diborane in tetrahydrofuran 398,410,430,745,852,1025,1590,1609,1793,1833.1877-1884 9-borabi-... 

Organoboranes are important in organic synthesis as reactive intermediates. Reactions have been developed by which the boron atom may be replaced by a wide variety of functional groups, such as —H, —OH, —NH2, —Br, —1, and —COOH.The present experiment demonstrates the conversion of an organoborane to an alcohol by oxidation with alkaline hydrogen peroxide. It is not necessary to isolate the organoborane prior to its oxidation. This simplification is particularly fortuitous in this case, since most alkylboranes, when not in solution, are pyrophoric (spontaneously flammable in air). 

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