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Volumn , Issue , 2006, Pages 37-71

Vinylaziridines in Organic Synthesis

Author keywords

Aziridines; Cycloaddition; Direct synthesis of vinylaziridines 1 ; Electron transfer to vinylaziridines; Epoxides; Isomerization; Nucleophiles; Organic synthesis; Rearrangement; Ring opening reactions; Vinylaziridines

Indexed keywords


EID: 84891040700     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527607862.ch2     Document Type: Chapter
Times cited : (18)

References (150)
  • 1
    • 0007988904 scopus 로고
    • General methods that can be widely applied for the synthesis of various aziri-dines and not only for vinylaziridines are not included in this section. Furthermore, although synthesis of vinylaziridines is often accomplished by formation of a carbon-carbon double bond after the aziri-dine ring has been formed, this type of synthetic route is not within the category of "direct synthesis of vinylaziridines". For examples, see:
    • General methods that can be widely applied for the synthesis of various aziri-dines and not only for vinylaziridines are not included in this section. Furthermore, although synthesis of vinylaziridines is often accomplished by formation of a carbon-carbon double bond after the aziri-dine ring has been formed, this type of synthetic route is not within the category of "direct synthesis of vinylaziridines". For examples, see: D. Borel, Y. Gelas-Mialhe, R. Vessiére, Can. J. Chem. 1976, 54, 1582;
    • (1976) Can. J. Chem. , vol.54 , pp. 1582
    • Borel, D.1    Gelas-Mialhe, Y.2    Vessiére, R.3
  • 22
    • 3242750572 scopus 로고    scopus 로고
    • telluronium allylides can react with N-Boc-aliphatic imines to afford is-vinyla-ziridines stereoselectively; see
    • telluronium allylides can react with N-Boc-aliphatic imines to afford is-vinyla-ziridines stereoselectively; see W.-W. Liao, X.-M. Deng, Y. Tang, Chem. Com-mun. 2004, 1516-1517.
    • (2004) Chem. Com-mun. , pp. 1516-1517
    • Liao, W.-W.1    Deng, X.-M.2    Tang, Y.3
  • 86
    • 0010426505 scopus 로고
    • a related reaction of [2-(aziridin-1-yl)alkenyl]triphenylphos-phonium bromides was also reported; see
    • a related reaction of [2-(aziridin-1-yl)alkenyl]triphenylphos-phonium bromides was also reported; see M. A. Calcagno, E. E. Schweizer, J. Org. Chem. 1978, 43, 4207-4215;
    • (1978) J. Org. Chem. , vol.43 , pp. 4207-4215
    • Calcagno, M.A.1    Schweizer, E.E.2
  • 87
    • 0009671050 scopus 로고
    • a related azepine formation through addition of N-unsubstituted azidirines to electrophilic carbon-carbon multiple bond systems such as acrylonitrile followed by aza-[3, 3]-Claisen rearrangement was reported by Hassner:
    • a related azepine formation through addition of N-unsubstituted azidirines to electrophilic carbon-carbon multiple bond systems such as acrylonitrile followed by aza-[3, 3]-Claisen rearrangement was reported by Hassner: A. Hassner, R. D'Costa, A. T. McPhail, W. Butler, Tetrahedron Lett. 1981, 22, 3691-3694;
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3691-3694
    • Hassner, A.1    D'Costa, R.2    McPhail, A.T.3    Butler, W.4
  • 145
    • 84891007288 scopus 로고    scopus 로고
    • For synthesis by dehydrobromination of 2-(1-bromovinyl)aziridines, see: Ref. [34].
    • For synthesis by dehydrobromination of 2-(1-bromovinyl)aziridines, see: Ref. [34].
  • 146
    • 0033550244 scopus 로고    scopus 로고
    • For synthesis by treatment of imines with nucleophiles, see:
    • For synthesis by treatment of imines with nucleophiles, see: F. Chemla, V. Hebbe, J. F. Normant, Tetrahedron Lett. 1999, 40, 8093-8096;
    • (1999) Tetrahedron Lett. , vol.40 , pp. 8093-8096
    • Chemla, F.1    Hebbe, V.2    Normant, J.F.3
  • 149
    • 0035954878 scopus 로고    scopus 로고
    • For synthesis by intramolecular amination of bromoallenes, see:
    • For synthesis by intramolecular amination of bromoallenes, see: H. Ohno, H. Hamaguchi, T. Tanaka, Org. Lett. 2001, 3, 2269-2271;
    • (2001) Org. Lett. , vol.3 , pp. 2269-2271
    • Ohno, H.1    Hamaguchi, H.2    Tanaka, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.