Synthesis of New Unsaturated Amines by The Stevens Rearrangement

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作者
M. O. Manukyan
A. Kh. Gyulnazaryan
A. V. Babakhanyan
A. A. Shahkhatuni
K. S. Barseghyan
机构
[1] National Academy of Sciences of Armenia,Institute of Organic Chemistry of Scientific
[2] Armenian State Pedagogical University after Kh. Abovyan,Technological Center of Organic and Pharmaceutical Chemistry
[3] National Academy of Sciences of the Republic of Armenia,Scientific
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关键词
1-(prop-2-yn-1-yloxy)-4-chlorobut-2-ene; -dimethyl-4-(prop-2-yn-1-yloxy)but-2-enyl-1-amine; Stevens 3,2-rearrangement; unsaturated tertiary amines;
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摘要
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.
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页码:325 / 329
页数:4
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