Name: 5,6-Dihydro-2H-pyran-2-one. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5,6-Dihydro-2H-pyran-2-one, is researched, Molecular C5H6O2, CAS is 3393-45-1, about Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines. Author is Haut, Franz-Lucas; Feichtinger, Niklas J.; Plangger, Immanuel; Wein, Lukas A.; Mueller, Mira; Streit, Tim-Niclas; Wurst, Klaus; Podewitz, Maren; Magauer, Thomas.
Authors present a modular, synthetic entry to polysubstituted pyrroles employing readily available 2,5-dihydrothiophenes. Ring-opening of the heterocycle provides access to a panel of 1,3-dienes which underwent pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The transformation is conducted in an open flask and proceeds at ambient temperatures (23°) in nondry solvents. A careful adjustment of the electronics and sterics of the 1,3-diene precursor allows for the isolation of key intermediates. DFT studies identified a reaction mechanism that features a 6π-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.
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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI