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Title
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Synthesis of 3-methoxyazetidines via an aziridine to azetidine rearrangement and theoretical rationalization of the reaction mechanism
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Author
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Abstract
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| The synthetic utility of N-alkylidene-(2,3-dibromo-2-methylpropyl)amines and N-(2,3-dibromo-2-methylpropylidene)benzylamines was demonstrated by the unexpected synthesis of 3-methoxy-3-methylazetidines upon treatment with sodium borohydride in methanol under reflux through a rare aziridine to azetidine rearrangement. These findings stand in contrast to the known reactivity of the closely related N-alkylidene-(2,3-dibromopropyl)amines, which are easily converted into 2-(bromomethyl)aziridines under the same reaction conditions. A thorough insight into the reaction mechanism was provided by both experimental study and theoretical rationalization. |
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Language
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English
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Source (journal)
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The journal of organic chemistry. - Washington, D.C., 1936, currens
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Publication
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Washington, D.C.
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2011
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ISSN
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0022-3263
[print]
1520-6904
[online]
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DOI
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10.1021/JO102555R
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Volume/pages
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76
:7
(2011)
, p. 2157-2167
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ISI
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000288692000020
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Full text (Publisher's DOI)
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