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21st August 2013 @ 10:35

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Reaction information

*#Reaction file
reactionscheme_47.cdx
*Reaction file type CDX
*Procedure Following the procedure reported by Whistler, the bis-tosylate, trans-O,O’-Cyclohexane-1,4-diylbis(methylene)toluensulfonate (905 mg, 2.00 mmol) and potassium thiolacetate (594 mg, 5.20 mmol, 2.60 eq) were reacted in 4 mL of acetone. Work-up and evaporation of the solvent yielded the crude product (brownish solid, 485 mg, purity 95% including the cis-contaminant, reaction yield 79%); this was dissolved in Et2O and treated with decolourizing charcoal. The yellow solid obtained (396 mg) was recrystallized twice in cold EtOH/H2O (flakes) to yield the pure product (white waxy solid, 52 mg, 0.20 mmol, yield 10%; purity > 95% trans-isomer). Rf 0.69 (UV 254 nm; 4/1 Et20/hexane).
*Yield (%) 10 %
*Type of Yield Isolated pure product
Reference(s)

PhD Thesis - 16Sep2010_final p25.pdf
PhD Thesis - 16Sep2010_final p134-135.pdf

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

Further information Compound 47: trans-S,S’-cyclohexane-1,4-diylbis(methylene)diethanethioate

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 45: Bistosylation: trans-O,O’-cyclohexane-1,4-diylbis(methylene)toluensulfonate
For step in multistep reaction - link to following reaction step  
Attached Files
reactionscheme_47.cdx
PhD Thesis - 16Sep2010_final p134-135.pdf