Publication
Title
Syntheses and reactions of 1-amino-2,2-dialkylcyclopropane-1-carbonitriles and -carboxamides : potential precursors of ACC derivatives
Author
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.
Language
English
Source (journal)
European journal of organic chemistry. - Weinheim
Publication
Weinheim : 1999
ISSN
1434-193X
Volume/pages
1(1999), p. 239-250
ISI
000077978100034
UAntwerpen
Faculty/Department
Publication type
Subject
External links
Web of Science
Record
Identification
Creation 28.01.2013
Last edited 08.10.2017