A Theoretical and Experimental Study on Acid-Catalyzed Isomerization of 1-Acylaziridines to the Oxazolines. Reexamination of a Possible SNi Mechanism by Using ab Initio Molecular Orbital Calculations

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3081-3088

  Hori, Kenzi ^a   Nishiguchi, Takeshi ^b   Nabeya, Aiko ^c  

^a KYUSHU UNIVERSITY   (Japan)

^b YAMAGUCHI UNIVERSITY   (Japan)

^c Tsurumi University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001283016     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961089n     Document Type: Article

References (37)

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24. +) with the broken three-membered ring. Although we tried to optimize this intermediate by using several initial geometries, we failed to optimize it and obtained the product with a five-membered ring. This result suggests that the there is no tight ion-pair intermediate with a broken three-membered ring.
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32. 1/2 Bohr units is a measure of the distance of a molecular configuration from the TS. See ref 12a.
33. Ni mechanism. The addition of diffuse functions does not cause any differences in the rank ordering of relative energies.
34. -1. The diffuse functions do not cause any serious differences, either.
35. -1 from the gas phase value. Therefore, the potential profiles including solvent effect is not largely different from those without the solvent effect.
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37. 3 of 6 was shifted to lower field in the presence of 7. Such a tendency was found to be pronounced when the ratio of 7/6 is large and the concentration of the solution is high.