Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 57, Pages 13083-13087Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903228
Keywords
density functional calculations; domino reactions; pericyclic reactions; ring expansion; sulfur heterocycles
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Funding
- Spanish Ministerio de Ciencia, Innovacion y Universidades [CTQ2016-76794-P, CTQ2016-80375-P, CTQ2014-51912-REDC]
- Consejera de Empleo, Industria y Turismo del Principado de Asturias [IDI/2018/000231]
- Basque Government/Eusko Jaurlaritza [IT-324-07]
- Spanish Ministerio de Ciencia, Innovacion y Universidades (FPU-predoctoral grant)
- FEDER [CTQ2016-76794-P, CTQ2016-80375-P, CTQ2014-51912-REDC]
- FEDER (FPU-predoctoral grant)
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Chlorosulfate derivatives are interesting reagents that have been traditionally used to get other sulfur-containing compounds by formal nucleophilic substitution of the chlorine atom. This work describes a different mode of reactivity of alkyne-containing chlorosulfates to get sultones, the sulfur analogues of lactones. The complex skeletal rearrangement observed in this transformation is comparable to those intricate processes promoted or catalyzed by organometallic compounds. However, the reaction here described does not require any reagent or additive, being just a thermal process. Computational calculations support a mechanism based on a series of cascade reactions where almost every step is counterintuitive. Some of these steps include original processes related to classical reactions, thus adding complementary views to traditional organic chemistry.
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