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Synthesis of Sultones from Chlorosulfates by a Complex Cascade Reaction Occurring under Mild Thermal Conditions
Author(s) -
Cala Lara,
Rivilla Iván,
Cossío Fernando P.,
Fañanás Francisco J.,
Rodríguez Félix
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903228
Subject(s) - chemistry , reagent , sulfur , nucleophile , reactivity (psychology) , computational chemistry , combinatorial chemistry , cascade , organic chemistry , nucleophilic substitution , catalysis , medicine , alternative medicine , pathology , chromatography
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.