Syntheses and reactions of 1-amino-2,2-dialkylcyclopropane-1-carbonitriles and -carboxamides - Potential precursors of ACC derivatives
(1999) European Journal of Organic Chemistry — n° 1, p. 239-250 (1999)
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- 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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Aelterman, W., Declercq, J.-P., Tehrani, K., Coppens, W., Huybrechts, T., De Kimpe, N., & Tourwe, D. (1999). Syntheses and reactions of 1-amino-2,2-dialkylcyclopropane-1-carbonitriles and -carboxamides - Potential precursors of ACC derivatives. European Journal of Organic Chemistry, 1, 239-250. https://doi.org/10.1002/(SICI)1099-0690(199901)1999:1<239::AID-EJOC239>3.0.CO;2-Z (Original work published 1999)