Synthesis and Reactions of Functionally Substituted 2-(Adamantan-1-yl)oxiranes View Full Text


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Article Info

DATE

2020-04

AUTHORS

M. V. Leonova, L. P. Permyakova, M. R. Baimuratov, Yu. N. Klimochkin

ABSTRACT

Functionally substituted oxiranes were synthesized by epoxidation of unsaturated compounds of the adamantane series with m-chloroperoxybenzoic acid. Adamantyl-substituted epibromohydrins reacted with nitrogen, oxygen, and sulfur nucleophiles to give only halogen substitution products. 2-(Adamantan-1-yl)-3-hydroxypropanoic acid was obtained by the reaction of 2-(adamantan-1-yl)-2-(bromomethyl)oxirane with 98% nitric acid. Acid-catalyzed ring opening of aminomethyloxiranes afforded trifunctional derivatives, adamantane-containing aminohalohydrins. Treatment oftrans-2-(adamantan-1-yl)-2-(phenylsulfanylmethyl)oxirane withn-butyllithium gave rise to a mixture ofZ and E isomers of 1-(adamantan-1-yl)-3-(phenylsulfanyl)prop-2-en-1-ol, whereas trans-2-(adamantan-1-yl)-3-(phenoxylmethyl)oxirane under similar conditions was converted to (E)-3-(adamantan-1-yl)prop-2-enal. More... »

PAGES

631-644

References to SciGraph publications

  • 2017-09. Organic chemistry. History and mutual relations of universities of Russia in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2014-02. Reaction of adamantane series olefins with N-bromosuccinimide in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2018-07. Synthesis and Transformations of Aryl-Substituted Alkenes of the Adamantane Series in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2014-04. Synthesis and thermal transformations of allyl aryl ethers of adamantane series in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
  • 2018-11. Synthesis and Transformations of 2-(Adamantan-1-yl)aziridine in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
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    http://dx.doi.org/10.1134/s1070428020040119

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