Journal
CHEMICAL COMMUNICATIONS
Volume 56, Issue 82, Pages 12395-12398Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc04896h
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- University of Turin
- Fondazione RiMed (Palermo, Italy)
- University of Vienna
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A sequential C1-homologation-nucleophilic substitution tactic is presented for the preparation of rare unsymmetrical dithioacetals. The judicious selection of thiosulfonates as convenient sulfur electrophilic sources - upon the homologation event conducted on an intermediate alpha-halothioether - guarantees the release of the non-reactive sulfonate group, thus enabling the subsequent nucleophilic displacement with an external added thiol [(hetero)aromatic and/or aliphatic]. Uniform high yields and excellent chemocontrol were deduced during the extensive scope study, thus documenting the versatility of the direct technique for the preparation of these unique and manipulable materials.
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