Mesoionic 1,3-oxazolium-5-olates (manchnones) react with thiocoumarins having an electron-withdrawing group at the 3-position to afford stereodefined fused polycyclic thienopyrroles. The reaction sequence seems to be triggered by a regiospecific dipolar cycloaddition followed by ring opening of the initial 1:1 cycloadduct and intramolecular rearrangement with an unusual ring contraction.
Titolo: | Stereodefined ring contraction-rearrangement of thiocoumarins to new fused benzo[b]thiophene derivatives |
Autori: | |
Data di pubblicazione: | 2011 |
Rivista: | |
Abstract: | Mesoionic 1,3-oxazolium-5-olates (manchnones) react with thiocoumarins having an electron-withdrawing group at the 3-position to afford stereodefined fused polycyclic thienopyrroles. The reaction sequence seems to be triggered by a regiospecific dipolar cycloaddition followed by ring opening of the initial 1:1 cycloadduct and intramolecular rearrangement with an unusual ring contraction. |
Handle: | http://hdl.handle.net/11570/1904860 |
Appare nelle tipologie: | 14.a.1 Articolo su rivista |
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