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Reversible Generation of Metastable Enols in the 1,4-Addition of Thioacetic Acid to alpha,beta-Unsaturated Carbonyl Compounds.
MedLine Citation:
PMID:  23164060     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Lukas Hintermann; Aleksej Turockin
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-20
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-20     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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