Reaction of 1-hydroxy-5-phenyltetrazole with olefin oxides
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1-Hydroxy-5-phenyltetrazole adds to ethylene oxide and propylene oxide to give the products of O- and N-β-oxyalkylation in 2∶1 ratio.
Propylene oxide is opened by 1-hydroxy-5-phenyltetrazole predominantly at the sterically most available carbon atom; this direction is favored by a 3∶1 ratio.
The product of the O-β-oxyalkylation of 1-hydroxy-5-phenyltetrazole upon treatment with a strong base regenerates the initial N-hydroxytetrazole and, thus, the O-β-hydroxyalkyl-ation of N-hydroxytetrazoles may serve to protect the N-hydroxyl group in these compounds.
KeywordsOxide Ethylene Propylene Carbon Atom Olefin Oxide
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