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.
Site- and Regioselectivity of Nitrile Oxide-Allene Cycloadditions : DFT-Based Semiquantitative Predictions / G. Molteni, A. Ponti. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 82:19(2017 Oct 06), pp. 10710-10714. [10.1021/acs.joc.7b01866]
Site- and Regioselectivity of Nitrile Oxide-Allene Cycloadditions : DFT-Based Semiquantitative Predictions
G. MolteniPrimo
;A. Ponti
Ultimo
2017
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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