Re-examination of the Claimed Isolation of Stable Noncyclic 1,2-Disulfoxides.

Autor: Block E; Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States., Cotelesage JJH; Molecular and Environmental Sciences Group, Department of Geological Sciences, University of Saskatchewan, Saskatoon, Saskatchewan S7N 5E2, Canada., Dikarev E; Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States., Garosi B; Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States., George GN; Molecular and Environmental Sciences Group, Department of Geological Sciences, University of Saskatchewan, Saskatoon, Saskatchewan S7N 5E2, Canada., Musah RA; Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States., Vogt LI; Molecular and Environmental Sciences Group, Department of Geological Sciences, University of Saskatchewan, Saskatoon, Saskatchewan S7N 5E2, Canada., Wei Z; Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States., Zhang Y; Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Nov 15; Vol. 26 (45), pp. 9619-9624. Date of Electronic Publication: 2024 Sep 04.
DOI: 10.1021/acs.orglett.4c02849
Abstrakt: Re-examination of the claimed isolation and X-ray characterization of di- p -tolyl and dimesityl 1,2-disulfoxides from thermolysis of the corresponding aryl sulfinimines and thiosulfinates showed that the isolated disulfide dioxides are instead the well-known isomeric thiosulfonates, as confirmed by XAS, DART-MS, X-ray, IR and NMR methods. Concerns with the original X-ray structures are addressed. Our results agree with the DFT prediction of very weak diaryl 1,2-disulfoxide S-S bond dissociation enthalpies. For now, room-temperature-stable noncyclic 1,2-disulfoxides remain unknown.
Databáze: MEDLINE