Journal
JOURNAL OF SULFUR CHEMISTRY
Volume 41, Issue 6, Pages 672-700Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/17415993.2020.1780237
Keywords
Thiocarbonyl compounds; electrophilic carbenes; nucleophilic carbenes; carbenoids; sulfur heterocycles
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Funding
- National Science Center (Cracow, Poland) [UMO-2016/23/G/ST5/04115/1]
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A variety of cyclic and acyclic products are reported for reactions of thiocarbonyl compounds with carbenes and their metal complexed derivatives. Electrophilic and nucleophilic carbenes react with non-enolizable thioketones yielding thiocarbonyl ylides or 1,3-zwitterions, respectively, as plausible, reactive intermediates. In most cases, the initially formed intermediates undergo 1,3-electrocyclization yielding respective thiiranes, which, depending on the substitution pattern, are either isolated as final products or extrude elemental sulfur forming substituted ethylene derivatives. In addition, reactive thiocarbonyl ylides formed from alpha-oxo substituted carbenoids after the thiophilic attack onto the C = S bond undergo competitive 1,3- versus 1,5-dipolar electrocyclization leading to thiiranes or 1,3-oxathioles, respectively. From the point of view of potential practical applications (coordination chemistry, organometallic chemistry, polymer chemistry), zwitterionic hetarylidene dithiocarboxylates accessible as stable 1:1 adducts from the reactions of nucleophilic heterocyclic carbenes (NHCs) with carbon disulfide are of great interest.
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