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


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.

SUBMITTER: Block E 

PROVIDER: S-EPMC11574841 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature

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

Block Eric E   Cotelesage Julien J H JJH   Dikarev Evgeny E   Garosi Benedetta B   George Graham N GN   Musah Rabi A RA   Vogt Linda I LI   Wei Zheng Z   Zhang Yuxuan Y  

Organic letters 20240904 45


Re-examination of the claimed isolation and X-ray characterization of di-<i>p</i>-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 dissoci  ...[more]

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