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Volumn 68, Issue 2, 2003, Pages 412-420

A theoretical study of the mechanisms and regiochemistry of the reactions of 5-alkoxyoxazole with thioaldehydes, nitroso compounds, and aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSITIONS; NITROGEN COMPOUNDS; RING OPENING POLYMERIZATION;

EID: 0037462406     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026330e     Document Type: Article
Times cited : (12)

References (68)
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    • note
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    • note
    • 4 to Y are much higher in energies than their corresponding Diels-Alder TSs (see Figure S12 in the Supporting Information).
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    • note
    • 298 (see Supporting Information for the energies and structures of DA TS 9 and adduct 10).
  • 55
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    • note
    • An interesting feature worthy of note is that the cis-3-thiazoline 4 is more stable than trans-3-thiazoline 8 by about 0.4 kcal/mol. So is the 3-oxazoline which has the cis-3-oxazoline being more stable than trans-3-oxazoline by about 0.4 kcal/mol, too. The reason for this cis preference is probably the electronic attraction between the two groups.
  • 56
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    • note
    • 3.5a This path can be easily excluded, owing to the high activation energy of 30.2 kcal/mol needed to generate the ylide 16 (see Figure S7 in Supporting Information). In terms of free energy, the pseudopericyclic TS 15 is still higher than the rate-determining TS 1 in the manifold A by about 8 kcal/mol. Furthermore, the ylide is a species lying higher in energy than the reactants by around 20.6 kcal/mol, suggesting that the backward ring-closing reaction converting ylide to oxazole is more efficient.
  • 59
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    • note
    • 1 bond.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.