1. Adamantylation of N-aryl and N-arylalkyl acetamides in trifluoroacetic acid.
- Author
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Novakov, I. A., Orlinson, B. S., Zavyalov, D. V., Porkhun, V. I., Savelyev, E. N., Potaenkova, E. A., Vostrikova, O. V., Nakhod, M. A., Kireeva, A. V., and Pichugin, A. M.
- Subjects
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TRIFLUOROACETIC acid , *ACETAMIDE , *ADAMANTANE derivatives , *ALKYL group , *ACETANILIDES , *ACID derivatives , *REGIOSELECTIVITY (Chemistry) - Abstract
Alkylation of N-aryl and N-arylalkyl acetamides with hydroxy adamantane derivatives in trifluoroacetic acid was studied. The differentiating effect of trifluoroacetic acid on the regio-selectivity of adamantylation of o-alkyl-substituted acetanilides was established, leading to energetically more stable products of para-substitution with respect to the alkyl group (the content of para-alkyl isomers is 93–94%). This enabled the synthesis of adamantylaminoarenes in 83–99% yields and with 95–99% purity. [ABSTRACT FROM AUTHOR]
- Published
- 2020
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