Adamantylazoles: XI. Reaction of 1-phenyltetrazole-5-thione with adamantan-1-ol in strong acids |
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| Authors: | A. V. Logvinov V. V. Saraev I. N. Polyakova Yu. A. Strelenko E. L. Golod |
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| Affiliation: | (1) St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia;(2) Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia;(3) Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia |
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| Abstract: | The reaction of 1-phenyltetrazole-5-thione with adamantan-1-ol in sulfuric acid gave 3-(1-adamantyl)-1-phenyltetrazole-5-thione having a mesoionic structure, 5-(1-adamantylsulfanyl)-1-phenyltetrazole, and 3-(1-adamantyl)-5-(1-adamantylsulfanyl)-1-phenyltetrazolium hydrogen sulfate. Hydrolysis of 5-(1-adamantylsulfanyl)-1-phenyltetrazole led to the formation of 1-phenyltetrazol-5-one. The adamantylation process is reversible. |
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