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Volumn 48, Issue 4, 1992, Pages 669-682

Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes

Author keywords

[No Author keywords available]

Indexed keywords

NITROXIDE DERIVATIVE; OXAZOLINE DERIVATIVE;

EID: 0026567914     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)88127-8     Document Type: Article
Times cited : (17)

References (47)
  • 13
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    • Extension of a perturbation molecular orbitals model to the study of regioselectivity in 1,3-dipolar cycloadditions: reactions of 3,5-dichloro-2,4,6-trimethylbenzonitrile oxide with heteroaromatic systems
    • There is a detailed theoreticaly well-founded discussion in particular for the cycloaddition of the relataed nitrile oxides.
    • (1991) Journal of the Chemical Society, Perkin Transactions 2 , pp. 1243
    • Bonati1    Benincori2    Zecchi3    Pitea4
  • 14
    • 84985638315 scopus 로고
    • PMO Analysis of Cycloadditions, III1). Regioselectivity and Reactivity in Cycloadditions of Formonitrile Oxide
    • (1987) Chemische Berichte , vol.120 , pp. 1471
    • Sustmann1    Sicking2
  • 15
    • 84918225088 scopus 로고    scopus 로고
    • See for instance 2c, 2f, .
  • 16
    • 84918225087 scopus 로고    scopus 로고
    • See for instance 3b, .
  • 26
    • 84921746503 scopus 로고
    • 1.3-Dipolare Cycloadditionen, XLVII. Reaktionen heteroaromatischer Aminoxide mit Carbonestern der Äthylen- und Acetylenreihe
    • Similar ring opening reactions are described:
    • (1969) Chemische Berichte , vol.102 , pp. 915
    • Huisgen1    Seidl2    Wulff3
  • 28
    • 84982067414 scopus 로고
    • Empirical Substituent Parameters forE/Z Equilibrium Constants
    • Compare also:
    • (1980) Chemische Berichte , vol.113 , pp. 2441
    • Knorr1
  • 29
    • 84918225085 scopus 로고    scopus 로고
    • A parallel situation is found for reaction of ethyl propiolate with N-cyclopropylmethyle-methylamine N-oxide (aldonitrone) and N-[(dicyclopropyl)methylene]-methylamine N-oxide (ketonitrone), respectively. See ref. 2c.
  • 31
    • 3042815080 scopus 로고
    • Usually the N-hydroxy enamine tautomers can be directly detected only if they are stabilized by additional functional groups:
    • (1980) Tetrahedron Lett. , vol.21 , pp. 3447
    • Reamer1    Sletzinger2    Shinkai3
  • 33
    • 84984275901 scopus 로고
    • Der Einfluß sterischer und elektronischer Faktoren auf die Stabilität von Aldonitronen und ihre Umwandlung in Isoxazolidine
    • (1986) Chemische Berichte , vol.119 , pp. 18
    • Aurich1    Eidel2    Schmidt3
  • 40
    • 33751553196 scopus 로고
    • 1H NMR data given in a recent publication differ somewhat from those found by us. In particular, no different signals are given for the two different methyl groups.
    • (1990) J. Org. Chem. , vol.55 , pp. 1736
    • Murahashi1    Mitsui2    Shiota3    Tsuda4    Watanabe5
  • 42
    • 84918225083 scopus 로고    scopus 로고
    • All NMR dates are given in Tables 3–6.
  • 43
    • 84984275901 scopus 로고
    • Der Einfluß sterischer und elektronischer Faktoren auf die Stabilität von Aldonitronen und ihre Umwandlung in Isoxazolidine
    • (1986) Chemische Berichte , vol.119 , pp. 18
    • Aurich1    Eidel2    Schmidt3
  • 47
    • 84918225081 scopus 로고    scopus 로고
    • Clark, T., SCAMP 4.0, based on MOPAC 4.0 (QCPE program 506).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.