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Selective cleavage of C-benzotriazole bonds in the presence of C-O bonds is reported for the reductive lithiation of N-(α-alkoxybenzyl)benzotriazoles and N-(α-alkoxyallyl)benzotriazoles in a one-step or two-step process. Trapping of the intermediates with carbonyl compounds gave unsymmetrically protected 1,2 or 1,4-diols in moderate yields.
Bis(benzotriazolyl)methylbenzenes 1a,b were converted by excess lithium metal in the presence of ketones into the 1,3-diols 3a-g in moderate to good yields. However, similar treatment of 5 gave only the mono reduction products 6, 7. Compounds 1a,b reacted with 1 equivalent of diketone 8 to form olefins 10a,b.
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