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Title
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Syntheses and reactions of 1-amino-2,2-dialkylcyclopropane-1-carbonitriles and -carboxamides : potential precursors of ACC derivatives
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Author
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Abstract
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| The direct cyclization of 2-amino-4-chloro-3,3-dimethylbutanenitrile with potassium tert-butoxide in THF afforded 1-amino-2,2-dimethylcyclopropane-1-carbonitrile and a dimerization product. Various new cis- and trans-1-(teri-butylamino)-2-benzyl- 2-methylcyclopropane-carbonitriles and the corresponding cyclopropanecarboxamides have been synthesized, with focus on the isolation of the pure stereoisomeric cyclopropanecarboxamides. The relative configuration of the stereoisomers was established by X-ray crystallographic analysis of one of the model compounds. A new route to the latter functionalized cyclopropanes was developed by reaction of 1-methoxycyclopropylamines with potassium cyanide. Some remarkable rearrangements of 1-aminocyclopropane-1-carbonitriles into azetidine and oxazine derivatives via Favorskii-derived intermediates are reported. Various aspects of the chemistry of geminally functionalized cyclopropanes are discussed. |
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Language
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English
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Source (journal)
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European journal of organic chemistry. - Weinheim, 1998, currens
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Publication
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Weinheim
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1999
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ISSN
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1434-193X
[print]
1099-0690
[online]
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Volume/pages
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1
(1999)
, p. 239-250
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ISI
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000077978100034
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