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Volumn 64, Issue 18, 1999, Pages 6710-6716

Cycloadditions of 16-electron 1,3-dipoles with ethylene. A density functional and CCSD(T) study

Author keywords

[No Author keywords available]

Indexed keywords

DIAZOMETHANE; ETHYLENE OXIDE DERIVATIVE; NITRILE; NITRILE IMIDE; NITRILE OXIDE; NITRILE YLIDE; NITROUS OXIDE; UNCLASSIFIED DRUG;

EID: 0032888073     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990504j     Document Type: Article
Times cited : (82)

References (58)
  • 1
    • 0004717512 scopus 로고
    • Perhaps the most outstanding contribution has come from the brilliant work of Rolf Huisgen. His efforts have helped transform the 1,3-dipolar addition from an almost obscure phenomenon into a major reaction type. See: (a) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 562;
    • (1963) Angew. Chem., Int. Ed. Engl. , vol.2 , pp. 562
    • Huisgen, R.1
  • 42
  • 48
    • 0345559842 scopus 로고    scopus 로고
    • note
    • In this work, we use the term orientation complex to characterize the spatial arrangement of the reactants at the beginning of the bonding interaction. See ref 1.
  • 49
    • 0001412254 scopus 로고
    • Nevertheless, orientation complexes, as a result of van der Waals interactions, have recently been found for ozone and ethylene in the gas phase and were confirmed by ab initio calculations. See: (a) Gillies, C. W.; Gillies, J. Z.; Suenram, R. D.; Lovas, F. J.; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1991, 113, 2412.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2412
    • Gillies, C.W.1    Gillies, J.Z.2    Suenram, R.D.3    Lovas, F.J.4    Kraka, E.5    Cremer, D.6
  • 55
    • 0344697600 scopus 로고    scopus 로고
    • note
    • This may be denoted as HOMO-controlled (the interaction of the dipole HOMO with the dipolarophile LUMO is greatest). See ref 10.
  • 57
    • 0344697599 scopus 로고    scopus 로고
    • note
    • It is of interest to note that the cycloaddition of nitrile imine (CNN) is more favorable than that of diazomethane (NNC) as given in Table 2. The reason for this can also be traced back to the singlet-triplet splitting of these 1,3-dipoles. See Table 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.