Title
Syntheses and reactions of 1-amino-2,2-dialkylcyclopropane-1-carbonitriles and -carboxamides : potential precursors of ACC derivatives Syntheses and reactions of 1-amino-2,2-dialkylcyclopropane-1-carbonitriles and -carboxamides : potential precursors of ACC derivatives
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Weinheim ,
Subject
Chemistry
Source (journal)
European journal of organic chemistry. - Weinheim
Volume/pages
(1999) :1 , p. 239-250
ISSN
1434-193X
ISI
000077978100034
Carrier
E
Target language
English (eng)
Abstract
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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