Synthesis and Transformations of Aryl-Substituted Alkenes of the Adamantane Series


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Abstract

Aryl-substituted alkenes of the adamantane series, 1-[(Z,E)-3-phenylprop-2-en-1-yl]adamantane and 1-[(Z)-3-phenylprop-1-en-1-yl]adamantane, have been synthesized by the Wittig reaction. Their allylic bromination involves two concurrent reactions, radical substitution and raical addition. The different chemical behaviors of the aryl-substituted alkenes have been demonstrated in the Ritter reaction. Depending on the alkene structure and acid catalyst nature, the products are secondary amides, sulfonic acid derivatives, and homoadamantane γ-sultone.

About the authors

S. A. Savel’eva

Samara State Technical University

Author for correspondence.
Email: svetlana.saveleva9@yandex.ru
Russian Federation, ul. Molodogvardeiskaya 244, Samara, 443100

M. V. Leonova

Samara State Technical University

Email: svetlana.saveleva9@yandex.ru
Russian Federation, ul. Molodogvardeiskaya 244, Samara, 443100

M. R. Baimuratov

Samara State Technical University

Email: svetlana.saveleva9@yandex.ru
Russian Federation, ul. Molodogvardeiskaya 244, Samara, 443100

Yu. N. Klimochkin

Samara State Technical University

Email: svetlana.saveleva9@yandex.ru
Russian Federation, ul. Molodogvardeiskaya 244, Samara, 443100

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