Sulfinamide

The general chemical structure of a sulfinamide

Sulfinamide is a functional group in organosulfur chemistry with the formula RS(O)NR'2 (R and R' = organic substituent). With a sulfur-oxygen double bond as well as S-C and S-N single bonds, the compounds are chiral. Sulfinamides are amides of sulfinic acid (RS(O)OH).

Tert-Butanesulfinamide, p-toluenesulfinamide, and 2,4,6-trimethylbenzenesulfinamide have been obtained in optically pure form.[1][2][3] They are used in asymmetric synthesis.

Sulfinamides arise in nature by the addition of thiols to nitroxyl:

RSH + HNO → RS(O)NH2
Structure of p-tolylsulfinamide (tolS(O)NH2)), highlighting the pyramidal nature of the S center.[4]

References

  1. ↑ Fanelli, D. L.; Szewczyk, J. M.; Zhang, Y.; Reddy, G. V.; Burns, D. M.; Davis, F. A. (2000). "SULFINIMINES (THIOOXIMINE S-OXIDES): ASYMMETRIC SYNTHESIS OF METHYL (R)-(+)-β-PHENYLALANATE FROM (S)-(+)-N-(BENZYLIDENE)-p-TOLUENESULFINAMIDE". Organic Syntheses. 77: 50. ; Collective Volume, 10, p. 47
  2. ↑ Ruano, J. L.; Alemán, J.; Parra, A.; Cid, M. B. (2007). "PREPARATION OF N-p-TOLYLSULFONYL-(E)-1-PHENYLETHYLIDENEIMINE". Organic Syntheses. 84: 129.
  3. ↑ Ramachandar, T.; Wu, Y.; Zhang, J.; Davis, F. A. (2006). "(S)-(+)-2,4,6-TRIMETHYLBENZENESULFINAMIDE". Organic Syntheses. 83: 131.
  4. ↑ Eccles, K. S.; Morrison, R. E.; Daly, C. A.; O'Mahony, G. E.; Maguire, A. R.; Lawrence, S. E. (2013). "Co-crystallisation Through Halogen Bonding with Racemic or Enantiopure Sulfinamides". CrystEngComm. 15: 7571–7575. doi:10.1039/C3CE40932E.


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