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21st August 2013 @ 10:10

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Reaction information

*#Reaction file
reactionscheme_46.cdx
*Reaction file type CDX
*Procedure Following the procedure reported by Whistler, the bis-tosylate, cis-O,O’-Cyclohexane-1,4-diylbis(methylene)toluensulfonate (93 mg, 0.20 mmol) was dissolved in 1 mL of acetone in a 10 mL rbf. Potassium thiolacetate (59 mg, 0.52 mmol, 2.60 eq.) was added, and after stirring for 10 min at r.t. the suspension was heated to reflux temperature (65 °C) and left overnight. After cooling to r.t. the reaction mixture was filtered, and the inorganic residue was washed with Et2O once. The organic phase was washed with brine, dried over MgSO4, and evaporated to yield the crude brown oil (59 mg). This was dissolved in DCM and shaken with decolourizing charcoal; filtration and evaporation of the solvent afforded a yellow oil (37 mg, 0.14 mmol, reaction yield 71%; purity: 87% cis-isomer, the rest of the mass is mostly trans-isomer and by-products; the pure product is supposedly a clear oil or low Mp white solid). Rf 0.69 (UV 254 nm; 4/1 Et20/hexane).
*Yield (%) 71 %
*Type of Yield Reaction yield
Reference(s)

PhD Thesis - 16Sep2010_final p25.pdf
 
PhD Thesis - 16Sep2010_final p134.pdf

Whistler, R. L.; Campbell, C. S. J. Org. Chem. 1966, 31, 816-818

Further information Compound 46: cis-S,S’-Cyclohexane-1,4-diylbis(methylene)diethanetioate

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step Reaction 44: Bistosylation: cis-O,O’-cyclohexane-1,4-diylbis(methylene)toluensulfonate
For step in multistep reaction - link to following reaction step  
Attached Files
PhD Thesis - 16Sep2010_final p134.pdf
reactionscheme_46.cdx