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The synthesis and Diels-Alder reactions of (E)- and (Z)-1-methoxy-3-(phenylsulfinyl)-1,3-butadienes

Adams, Harry and Anderson, James C. and Bell, Richard and Neville Jones, D. and Peel, Michael R. and Tomkinson, Nicholas C. O. (1998) The synthesis and Diels-Alder reactions of (E)- and (Z)-1-methoxy-3-(phenylsulfinyl)-1,3-butadienes. Journal of the Chemical Society, Perkin Transactions 1 (23). pp. 3967-3974. ISSN 1472-7781

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Abstract

The mild and efficient generation of benzenesulfenic acid by the thermolysis of Et 2-ethoxycarbonyl-3-(phenylsulfinyl)butanoate in refluxing dichloromethane, its in situ trapping with (E)- and (Z)-1-methoxy-2-buten-3-yne to form (E)-1-methoxy-3-(phenylsulfinyl)-1,3-butadiene and (Z)-1-methoxy-3-(phenylsulfinyl)-1,3-butadienes resp. proceeds in high yield. The lithium perchlorate catalyzed Diels-Alder reaction of (E)-1-methoxy-3-(phenylsulfinyl)-1,3-butadiene with both sym. and unsym. carbonyl activated dienophiles proceeds with complete regioselectivity and in some cases complete endo-selectivity.