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The Strathprints institutional repository is a digital archive of University of Strathclyde research outputs.

Strathprints serves world leading Open Access research by the University of Strathclyde, including research by the Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), where research centres such as the Industrial Biotechnology Innovation Centre (IBioIC), the Cancer Research UK Formulation Unit, SeaBioTech and the Centre for Biophotonics are based.

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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.