Journal
RUSSIAN CHEMICAL BULLETIN
Volume 69, Issue 6, Pages 1096-1101Publisher
SPRINGER
DOI: 10.1007/s11172-020-2873-9
Keywords
adamantylation; adamantan-1-ol; acetanilide; N-benzylacetamide; trifluoroacetic acid; density functional theory; Gasteiger-Marsili method
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Funding
- Ministry of Higher Education and Science of the Russian Federation [4.3230.2017/4.6]
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Alkylation ofN-aryl andN-arylalkyl acetamides with hydroxy adamantane derivatives in trifluoroacetic acid was studied. The differentiating effect of trifluoroacetic acid on the regio-selectivity of adamantylation ofo-alkyl-substituted acetanilides was established, leading to energetically more stable products ofpara-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.
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