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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Re-examination of the Claimed Isolation of Stable Noncyclic 1,2-Disulfoxides
Eric Block1, Julien J H Cotelesage2, Evgeny Dikarev1
1Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States.
Abstract:
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.
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