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Title
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Synthesis of 4,4-disubstituted -lactams by regiospecific electrophile- and silver-induced ring expansion of 2,2-disubstituted 1-methoxycyclopropylamines
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Author
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Abstract
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| 2,2-Disubstituted 1-methoxycyclopropylamines underwent regiospecific ring expansion to 1,4,4-trisubstituted 2-azetidinones by N-chlorination with tert-butyl hypochlorite and subsequent rearrangement with silver tetrafluoroborate. Upon thermolysis, 4,4-disubstituted beta-lactams suffer a characteristic ring opening to afford beta,gamma-unsaturated carboxylic amides. The reduction of 1,4,4-trisubstituted 2-azetidinones with lithium aluminum hydride afforded 1,2,2-trisubstituted azetidines. |
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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.
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Publication
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Washington, D.C.
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1996
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ISSN
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0022-3263
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Volume/pages
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61
:19
(1996)
, p. 6500-6503
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ISI
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A1996VJ00600013
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Full text (Publisher's DOI)
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