Beilstein J. Org. Chem.2018,14, 2897–2906, doi:10.3762/bjoc.14.268
alcohols (ArSO2–CR1=CH–C(OH)R2R3, yields of 78–99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene1,1-dioxides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction
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-oxathiolium ions; thiochromene1,1-dioxides; Introduction
Allenes are widely
decided to achieve the selective formation of each of these different products, butadienes 3, adducts with nucleophiles 4, and thiochromene1,1-dioxides 5, from allenes 2. The preparation of compounds 3a–h was done by the following method (Scheme 3). Reactions of 2a–h were carried out in CH2Cl2 with 1
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Graphical Abstract
Scheme 1:
(Arylsulfinyl)allenes 1 and (arylsulfonyl)allenes 2 used in this study.