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Updated: Jun 17, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Ring-opening/ring-closing protocols from nitrothiophenes: six-membered versus unusual eight-membered sulfur
Lara Bianchi1, Gianluca Giorgi, Massimo Maccagno
1Dipartimento di Chimica e Chimica Industriale, Genova University, Via Dodecaneso 31, 16146 Genova, Italy.
Abstract:
When Ar is a low-aromaticity homo- or heterosystem, the sulfonyl-stabilized anion of nitrobutadienes 4 (which derive from the initial ring opening of 3-nitrothiophene) undergoes a rather surprising addition onto the aromatic ring itself, thereby leading to the construction of an unusual eight-membered sulfur heterocycle condensed with the original Ar ring. The competitiveness of such a pathway with respect to the formation of the thiopyran ring (i.e., addition onto the nitrovinyl moiety) is favored at low temperatures, thus revealing its nature as a kinetically controlled process.
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