Unexpected Cleavage of 2-Azido-2-(hydroxymethyl)oxetanes: Conformation Determines Reaction Pathway?

[摘要]：An unanticipated cleavage of 2-azido-2-(hydroxymethyl)oxetanes is reported In attempts to oxidize the title oxetanyl alcohols to the corresponding carboxylic acids with RuO4, cleaved nitriles were formed as the sole isolable products, while a closely related tetrahydrofuran gave solely the expected carboxylic acid Quantum chemical calculations suggest that the divergent outcomes are governed by conformational differences in the azidoalcohols

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