Synthesis of New Unsaturated Amines by The Stevens Rearrangement


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Abstract

Monoalkylation of 1,4-dichlorobut-2-ene with prop-2-yn-1-ol under phase-transfer catalysis conditions led to the formation of 1-(prop-2-yn-1-yloxy)-4-chlorobut-2-ene. The latter reacted with dimethylamine to afford N,N-dimethyl-4-(prop-2-yn-1-yloxy)but-2-enyl-1-amine. Its quaternization afforded new ammonium salts containing 4-(prop-2-yn-1-yloxy)but-2-enyl group. Unsaturated tertiary amines formed as a result of Stevens 3,2-rearrangement of quaternary salts.

About the authors

M. O. Manukyan

Institute of Organic Chemistry of Scientific-Technological Center of Organic and Pharmaceutical Chemistry

Author for correspondence.
Email: manukyanmeri@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

A. Kh. Gyulnazaryan

Institute of Organic Chemistry of Scientific-Technological Center of Organic and Pharmaceutical Chemistry

Email: manukyanmeri@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

A. V. Babakhanyan

Armenian State Pedagogical University after Kh. Abovyan

Email: manukyanmeri@gmail.com
Armenia, Yerevan

A. A. Shahkhatuni

Scientific-Technological Center of Organic and Pharmaceutical Chemistry

Email: manukyanmeri@gmail.com
Armenia, Yerevan

K. S. Barseghyan

Institute of Organic Chemistry of Scientific-Technological Center of Organic and Pharmaceutical Chemistry

Email: manukyanmeri@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014


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