Unexpected cleavage of 2-azido-2-(hydroxymethyl)oxetanes: conformation determines reaction pathway?
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.
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
Elisa
E
Farber
Jackson
J
Herget
José A
JA
Gascón
Amy R
AR
Howell
D001386:Azides / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D007700:Kinetics; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011789:Quantum Theory
D001386:Azides; D004988:Ethers, Cyclic; C005287:oxetane