Silver-mediated allylic disulfide rearrangement for conjugation of thiols in protic media

Journal of Organic Chemistry

Volumn 74, Issue 24, 2009, Pages 9422-9427

  Crich, David ^a,b   Subramanian, Venkataraman ^b   Karatholuvhu, Maheswaran ^b  

^a CNRS   (France)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC REARRANGEMENT; AMBIENT TEMPERATURES; CHEMICAL EQUATIONS; MEDIATED REACTIONS; PROTECTING GROUP; PROTIC SOLVENTS; ROOM TEMPERATURE; SILVER NITRATES; THIOPHILIC;

CHEMICAL REACTIONS; PHOSPHORUS COMPOUNDS;

SILVER;

DIALLYL DISULFIDE; PHOSPHINE DERIVATIVE; SILVER NITRATE; SOLVENT; THIOL DERIVATIVE;

ALLYLIC REARRANGEMENT; ARTICLE; CHEMICAL REACTION; CONJUGATION; DESULFURIZATION; ENVIRONMENTAL TEMPERATURE; ROOM TEMPERATURE; STOICHIOMETRY;

ALLYL COMPOUNDS; DISULFIDES; GLUTATHIONE; HYDROGEN-ION CONCENTRATION; MODELS, CHEMICAL; PHOSPHINES; PROTONS; SILVER; SILVER NITRATE; SOLVENTS; SULFHYDRYL COMPOUNDS; TEMPERATURE;

EID: 73149094534     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902012m     Document Type: Article

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30. Obtained by silylation of 3 under standard conditions with tert-butyldimethylsilyl chloride in 80% yield.
31. For all disubstituted alkenes, only the E-isomers were observed and isolated.