The Diels-Alder Reaction of 2,3-Disulfur-Substituted 1,3-Butadienes |
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Authors: | Shang-Shing P Chou Der-Jen Sun |
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Abstract: | The 2,3-disulfur-substituted 1,3-dienes (1) can be readily prepared from their stable 3-sulfolene precursors (2) by thermal extrusion of SO2. The Diels-Alder reaction of diene (1) with several dienophiles has been studied. The substituent effect on the reactivity and regioselectivity follows the order of PhS >PhSO >PhSO2. Lewis acid can greatly increase the regioselectivity of this reaction. The diene (1c), bearing a strong electron-withdrawing sulfonyl group, also reacted as a dienophile. |
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Keywords: | Sulfur-substituted dienes 3-sulfolenes the Diels-Alder reaction |
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