Summary
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1.
The hydrogen-exchange reaction of the tertiary araikyl alcoholss dimethylphenylcarbinol and 1-phenylcyclohexanol with anhydrous D3PO4 was studied. It was established that araikyl alcohols enter into hydrogen exchange much more slowly than do trialkylcarbinols.
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2.
The hydrogen-exchange reaction of the triarylcarbinols: triphenylcarbinol, di-p-tolylphenylcarbinol and m-tolyldiphenylcarbinol with anhydrous D2SO4 was studied. It was established that the indicated carbinols do not enter into hydrogen exchange with D2SO4 under the studied conditions.
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3.
The possible reasons for carbonium ions showing difficult hydrogen exchange were discussed.
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Literature cited
V. N. Setkina and D. N. Kursanov, Proc. Acad. Sci. USSR 109, 552 (1956).
N. C. Deno and W. L. Evans, J. Am. Chem. Soc. 78, 582 (1956).
A. Hantzsch, Ber. 54, 2573 (1921).
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Setkina, V.N., Kursanov, D.N. Study of hydrogen exchange of triarylgarbinols and arylalkylcarbinols with acids. Russ Chem Bull 8, 410–413 (1959). https://doi.org/10.1007/BF00917694
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DOI: https://doi.org/10.1007/BF00917694