| Reversible Generation of Metastable Enols in the 1,4-Addition of Thioacetic Acid to alpha,beta-Unsaturated Carbonyl Compounds. | |
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MedLine Citation:
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PMID: 23164060 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Addition of thioacetic acid to reactive alpha,beta-unsaturated carbonyl compounds like acrolein or crotonaldehyde in acetone-d6 generates metastable (E)- and (Z)-1-alkenols, which tautomerize slowly at ambient temperature. The 1,4-addition of thioacetic acid and crotonaldehyde to (Z)-3-(acetylsulfanyl)-1-propen-1-ol is reversible with Keq = 5.5 +/- 0.5 L/mol. A concerted, cyclic 1,4-addition mode is proposed to explain the preferred (Z)-stereoselectivity in lower polarity, non-protic solvents. |
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Authors:
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Lukas Hintermann; Aleksej Turockin |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-11-20 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2012 Nov |
Date Detail:
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Created Date: 2012-11-20 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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