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Volumn 64, Issue 42, 2008, Pages 9983-9988

Copper(0)-induced aminocyclopropanation of olefins via deselenation of N,N-disubstituted aromatic selenoamides

Author keywords

Aminocarbene species; Aminocyclopropane; Copper(0); Cyclopropanation; Deselenation; Selenoamide

Indexed keywords

1,4 DICARBONYL DERIVATIVE; ACRYLONITRILE; ALKENE DERIVATIVE; AMIDE; AMINOCYCLOPROPANE DERIVATIVE; AROMATIC COMPOUND; CARBONYL DERIVATIVE; COPPER; CYCLOPROPANE DERIVATIVE; HYDROCHLORIC ACID; N (SELENOBENZOYL)PIPERIDINE; SELENIUM DERIVATIVE; SELENOAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 50549096132     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.101     Document Type: Article
Times cited : (9)

References (106)
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    • note
    • In addition to the present aminocyclopropanation, we also observed deselenative coupling reaction and N-H bond insertion reaction by using selenoamides in the presence of Cu(0). These results strongly suggest the possibility of the intermediacy of α-aminocarbene or its related species. However, we could not succeed the direct observation of α-aminocarbene species. The alternative pathway may include the formation of radical anions from selenoamide by the action of Cu(0).
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    • note
    • Configurations of another aminocyclopropanes were determined by DIFNOE-NMR experiments. It was suggested that aminocyclopropanes mainly formed Z-configuration.
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    • note
    • The structures of aminocyclopropane- and aminocyclopentane-nitriles were determined by DIFNOE-NMR experiments.
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    • For reactions of cyclopropane with tetracyanoethylene (TCNE) to produce the corresponding cyclopentanes, see:
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    • note
    • The structure of aminocyclopropane, e.g., 4ak, was also determined by DIFNOE-NMR experiments. The result suggested that the piperidyl group was located with a Z-position to two ester groups.
  • 88
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    • note
    • E to Z isomerization was also observed with the isolated aminocyclopropanes, and this result strongly suggests that Z-isomers are thermodynamically more stable isomers in comparison with the corresponding E-isomers.
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  • 104


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.