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Chemical Transformations of Tetracyclo[3.3.1.1 3,7 .0 1,3 ]decane (1,3-Dehydroadamantane): IX. Noncatalytic Reactions with Alkylarenes
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-07-20 , DOI: 10.1134/s1070428020060123
G. M. Butov , V. M. Mokhov , E. A. Zubovich

Abstract

The reaction of 1,3-dehydroadamantane with alkylbenzenes was studied for the first time. It involved the C–H bond of the alkyl substituent in the α-position with respect to the aromatic ring. The proposed radical mechanism of the reaction was confirmed by the isolation of 1,1′-biadamantane and 1,2-diphenylethane derivatives. Difficultly accessible (adamantan-1-ylmethyl)arenes were synthesized in 53–78% yields.


中文翻译:

四环[3.3.1.1 3,7 .0 1,3]癸烷(1,3-脱氢金刚烷)的化学转化:IX。与炔烃的非催化反应

摘要

首次研究了1,3-脱氢金刚烷与烷基苯的反应。它涉及相对于芳香环的α位烷基取代基的CH键。通过分离1,1'-双金刚烷和1,2-二苯乙烷衍生物,证实了所提出的自由基反应机理。难以合成的(金刚烷-1-基甲基)芳烃的合成产率为53-78%。
更新日期:2020-07-20
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