Your browser does not fully support modern features. Please upgrade for a smoother experience.
Organosulfur Synthesis: History
Please note this is an old version of this entry, which may differ significantly from the current revision.
Subjects: Chemistry, Organic
Contributor: Helena Kang

Organosulfur synthesis comprises bond-forming and functional-group interconversion methods that produce organic compounds containing carbon–sulfur bonds or transform one organosulfur class into another. The concept is bounded by sulfur attached to an organic framework and excludes purely inorganic sulfur chemistry. Its defining reactivity follows sulfur across several oxidation states, including thiols, sulfides, disulfides, sulfoxides, sulfones, sulfonium salts, sulfur ylides, sulfinates, and sulfonates. Nucleophilic substitution by sulfur anions, electrophilic sulfur transfer, radical addition, and metal-catalyzed C–S coupling are principal bond-forming modes. Reactions at sulfur(IV) can change both oxidation state and connectivity through sulfoxide activation, sulfonium formation, ylide chemistry, and sulfinate conversion [1]. Sulfur-transfer reagents provide complementary routes in which a defined sulfur unit is delivered to an organic substrate [2]. The field is distinguished from organoselenium and organophosphorus synthesis by sulfur's characteristic oxidation-state ladder, nucleophilicity, and leaving-group behavior.

  • organosulfur compound
  • C–S bond formation
  • sulfur oxidation state
  • nucleophilic substitution

Sulfur-Based Synthesis Techniques • Organic Chemistry • Chemistry • Physical Sciences

References

  1. Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide; Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts. Chem. Rev. 2019, 119, 8701-8780, 10.1021/acs.chemrev.9b00111.
  2. Hui Liu; Xuefeng Jiang; Transfer of Sulfur: From Simple to Diverse. Chem. – Asian J. 2013, 8, 2546-2563, 10.1002/asia.201300636.
More
This entry is offline, you can click here to edit this entry!
Academic Video Service