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Title
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Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines
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Author
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Abstract
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| 3-(2-Chloroalkyl)-2,2-dihaloaziridines were synthesized via cycloaddition of dihalocarbenes to the C=N double bond of (3-chloroimines. Under the action of Lewis acids or HCl, N-C(3) bond cleavage occurred, giving rise to N-substituted 2,4-dichloro-3,3-dimethylbutanamides, which were further converted to 3-chloropyrrolidin-2-ones under alkaline conditions. When 2,2-dichloro-3-(2-chloro-1,1-dimethylethyl)-1-phenylaziridine was reacted with sodium methoxide, aziridine ring opening with N-C(2) bond cleavage took place, leading to methyl 4-chloro-3,3-dimethyl-2-(phenylamino)butanoate. (C) 2008 Elsevier Ltd. All rights reserved. |
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Language
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English
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Source (journal)
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Tetrahedron. - Oxford, 1957, currens
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Publication
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Oxford
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2008
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ISSN
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0040-4020
[print]
1464-5416
[online]
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DOI
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10.1016/J.TET.2008.05.121
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Volume/pages
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64
:32
(2008)
, p. 7524-7530
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ISI
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000257912200008
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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