Site- and Regioselectivity of Nitrile Oxide-Allene Cycloadditions: DFT-Based Semiquantitative Predictions.
J Org Chem
; 82(19): 10710-10714, 2017 10 06.
Article
em En
| MEDLINE
| ID: mdl-28849926
ABSTRACT
Nitrile oxide 1,3-dipolar cycloaddition to arylsulfonyl- and dialkylaminoallenes have been investigated within the framework of the Kohn-Sham density functional theory (DFT) at the B3LYP/6-31G(d,p) level. The hitherto-unexplained experimental behavior of sulfonylallenes was rationalized by transition-state calculations which enabled a semiquantitative treatment of the cycloaddition site- and regioselectivity. The reliability of DFT computations was further established by predicting the complete selectivity of the nitrile oxide cycloaddition to dialkylaminoallenes according to previous experimental findings.
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MEDLINE
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Prognostic_studies
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Risk_factors_studies
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En
Ano de publicação:
2017
Tipo de documento:
Article