5-Membered cyclic ethers via phenonium ion mediated cyclization through carbonate chemistry
Articolo
Data di Pubblicazione:
2018
Abstract:
Cyclization of 2-(2-hydroxyethyl)phenol via DMC chemistry in acidic conditions is herein discussed
for the first time. Reaction conditions have been investigated and optimized. This substrate is quite appealing
as it incorporates a 2-hydroxyethyl moiety in ortho to the aromatic hydroxyl group capable of stabilizing
the related phenonium ion. When the reaction mechanism was investigated via theoretical calculations, the
results suggest that the most favorable pathway encompasses a DMC-mediated formation of the phenonium
ion that is converted into the 2-(2-methoxyethyl)phenol. The related cyclic ether is then formed via intramolecular
cyclization of this intermediate. This peculiar cyclization reaction is another example of the versatility
of DMC herein used as solvent, methoxycarbonylation agent and leaving group in the intramolecular cyclization
leading to the phenonium ion.
Tipologia CRIS:
03A-Articolo su Rivista
Keywords:
anchimeric effect; computer modeling; cyclizations; dimethyl carbonate; green chemistry; ICGC-6; Chemistry (all); Chemical Engineering (all)
Elenco autori:
Aricã², Fabio; Maranzana, Andrea; Musolino, Manuele; Tundo, Pietro
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