22947-40-6Relevant articles and documents
Adamantylation of N-aryl and N-arylalkyl acetamides in trifluoroacetic acid
Kireeva, A. V.,Nakhod, M. A.,Novakov, I. A.,Orlinson, B. S.,Pichugin, A. M.,Porkhun, V. I.,Potaenkova, E. A.,Savelyev, E. N.,Vostrikova, O. V.,Zavyalov, D. V.
, p. 1096 - 1101 (2020/07/25)
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 93–94percent). This enabled the synthesis of adamantylaminoarenes in 83–99percent yields and with 95–99percent purity.
