Regioselective and Stepwise [8 + 2] Cycloaddition Reaction between Alkynyl–Fischer Carbene Complexes and Tropothione

The formal [8 + 2] cycloaddition reaction between alkynyl Fischer carbene complexes and tropothione leads to the regioselective formation of novel 3aH-cyclohepta[b]thiophene carbene complexes. Computational DFT calculations indicate that the process proceeds stepwise via antiaromatic zwitterionic in...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-08, Vol.77 (15), p.6648-6652
Main Authors: Rivero, Alexandra R, Fernández, Israel, Sierra, Miguel A
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
Thiones - chemistry
Thiophenes - chemical synthesis
Thiophenes - chemistry
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Summary:The formal [8 + 2] cycloaddition reaction between alkynyl Fischer carbene complexes and tropothione leads to the regioselective formation of novel 3aH-cyclohepta[b]thiophene carbene complexes. Computational DFT calculations indicate that the process proceeds stepwise via antiaromatic zwitterionic intermediates
ISSN:0022-3263
1520-6904
DOI:10.1021/jo3011304