Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 5, Pages 755-766Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800690
Keywords
alkyl halides; S-alkylisothiouronium salts; sodium dodecyl sulfate; thia-Michael addition; thioureas; water
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Funding
- Shiraz University Research Council
- TWAS chapter of Iran based at ISMO
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A pronounced catalytic. effect of sodium dodecyl sulfate (SDS) was observed on the in situ production of S-alkylisothiouronium salts via the reaction of primary, allyl and benzyl halides with thiourea in SDS droplets Hydrolysis of the generated S-alkylisothiouronium salts in the palisade layer of the droplets produces the corresponding thiol moieties which are immediately added to the electron-deficient olefins that are present in the micellar core to produce the thia-Michael adducts. The entire route is an almost odorless process. The yields of the products are good to excellent and the method is applicable to large-scale operation without any problem.
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