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Synthesis and reactions of 1-Amino-2, 2-dialkylcyclopropane-1-carbonitriles and -carboxamides: potential precursors of ACC derivatives

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Organization
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.
Keywords
(-)-(1S, ALPHA-CHLORO KETIMINES, 2R)-ALLONORCORONAMIC ACID, ETHYLENE BIOSYNTHESIS, AMINO-ACIDS, cyclopropanes, rearrangements, cyanohydrins, Schiff bases, small ring systems

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MLA
Aelterman, Wim, KA Tehrani, W Coppens, et al. “Synthesis and Reactions of 1-Amino-2, 2-dialkylcyclopropane-1-carbonitriles and -carboxamides: Potential Precursors of ACC Derivatives.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 1 (1999): 239–250. Print.
APA
Aelterman, W., Tehrani, K., Coppens, W., Huybrechts, T., De Kimpe, N., Tourwe, D., & Declercq, J. (1999). Synthesis 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.
Chicago author-date
Aelterman, Wim, KA Tehrani, W Coppens, Tom Huybrechts, Norbert De Kimpe, D Tourwe, and Jan Declercq. 1999. “Synthesis 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.
Chicago author-date (all authors)
Aelterman, Wim, KA Tehrani, W Coppens, Tom Huybrechts, Norbert De Kimpe, D Tourwe, and Jan Declercq. 1999. “Synthesis 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.
Vancouver
1.
Aelterman W, Tehrani K, Coppens W, Huybrechts T, De Kimpe N, Tourwe D, et al. Synthesis and reactions of 1-Amino-2, 2-dialkylcyclopropane-1-carbonitriles and -carboxamides: potential precursors of ACC derivatives. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 1999;(1):239–50.
IEEE
[1]
W. Aelterman et al., “Synthesis and reactions of 1-Amino-2, 2-dialkylcyclopropane-1-carbonitriles and -carboxamides: potential precursors of ACC derivatives,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no. 1, pp. 239–250, 1999.
@article{120681,
  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.},
  author       = {Aelterman, Wim and Tehrani, KA and Coppens, W and Huybrechts, Tom and De Kimpe, Norbert and Tourwe, D and Declercq, Jan},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {(-)-(1S,ALPHA-CHLORO KETIMINES,2R)-ALLONORCORONAMIC ACID,ETHYLENE BIOSYNTHESIS,AMINO-ACIDS,cyclopropanes,rearrangements,cyanohydrins,Schiff bases,small ring systems},
  language     = {eng},
  number       = {1},
  pages        = {239--250},
  title        = {Synthesis and reactions of 1-Amino-2, 2-dialkylcyclopropane-1-carbonitriles and -carboxamides: potential precursors of ACC derivatives},
  year         = {1999},
}

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