Beilstein J. Org. Chem.2018,14, 2897–2906, doi:10.3762/bjoc.14.268
, D2SO4), (arysulfonyl)allenes (ArSO2–CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO–CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathioliumions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl
mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2–CR1=CH–C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.
Keywords: (arylsulfinyl)allenes; (arylsulfonyl)allenes; butadienes; 1,2-oxathioliumions; thiochromene 1,1-dioxides; Introduction
Allenes are widely
to alcohols 7a,b.
Conclusion
Transformations of (arylsulfonyl)- and (arylsulfinyl)allenes under the action of the Brønsted superacid TfOH, or strong Lewis acids AlX3 (X = Cl, Br) have been studied. Under electrophilic conditions, these allenes form the corresponding 1,2-oxathioliumions, which have
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Graphical Abstract
Scheme 1:
(Arylsulfinyl)allenes 1 and (arylsulfonyl)allenes 2 used in this study.