A preparative scale reduction of alkyl disulfides with tributyl phosphine and water

Synthetic Communications

Volumn 29, Issue 3, 1999, Pages 351-358

  Ayers, Joshua T ^a   Anderson, Shelby R ^a  

^a TRINITY COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DI SEC BUTYL DISULFIDE; DIBENZYL DISULFIDE; DIBUTYLDISULFIDE; DIPHENYL DISULFIDE; DISULFIDE; FURFURYLDISULFIDE; PHOSPHINE DERIVATIVE; THIOESTER; THIOL DERIVATIVE; TRIBUTYLPHOSPHINE; UNCLASSIFIED DRUG; WATER;

ACYLATION; ARTICLE; BIOCHEMISTRY; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

EID: 0033025293     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919908085777     Document Type: Article

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23. The fact that the reductions were more rapid in pyridine raised the question as to whether pyridine may be acting as a sulfur transfer reagent. To test this possibility, one to five equivalents of pyridine or DMAP were added to the reaction in THF. The rate of reduction was not enhanced by the presence of these potential transfer catalysts.
24. The extent of reduction was determined by comparing the NMR ratios of unreacted disulfide to the thioester product.
25. Yields for the smaller, more volatile, butyl thiols/thioesters were significantly lower than those for the diphenyl and dibenzyl thioesters. This most likely reflects losses due to the evaporation of the volatile thiol intermediates and thioester products.
26. Acetyl chloride was also used but resulted in overall yields that were slightly lower.