Nitroarenes, allylboration

Allyl alcohol is here obtained in nearly quantitative yield, whereas its yield in the reaction of ArNCh with A113B does not exceed 5%. Consequently nitrosoarenes are not intermediates m the reductive allylboration of nitroarenes. 

A series of reactions of nitroarenes with triallyl-, trimethallyl- and tricrotylborane have been studied. It has been established that the major process is reductive allylboration of nitro-groups accompanied by an allylic rearrangement. As a result, a new convenient method of the synthesis of N-allylanilines has been elaborated. 

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