ol8b02979_si_001.pdf (7.56 MB)
π‑Extension of Strained Benzenoid Macrocycles Using the Scholl Reaction
journal contribution
posted on 2018-10-19, 23:55 authored by Nirob
K. Saha, Nirmal K. Mitra, Kara F. Johnson, Bradley L. MernerA series
of bent p-terphenyl-containing macrocycles
have been synthesized and then regioselectively brominated, arylated,
and subsequently subjected to a Scholl-based cyclodehydrogenation
reaction. Shortening the alkyloxy bridging unit of these macrocycles
increases the bend in the p-terphenyl unit, as well
as the strain energy (SE) of the central para-phenylene
ring system. For the first time, incremental increases in SE of the
macrocyclic structure of this class of benzenoid compounds have been
investigated in the context of π-extension to strained polycyclic
aromatic hydrocarbon systems using the Scholl reaction.
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terphenyl-containing macrocyclesseriesScholl-based cyclodehydrogenation reactionregioselectively brominatedparaScholl Reactionarylatedalkyloxybenzenoid compoundshydrocarbon systemspolycyclicterphenyl unitExtensionStrained Benzenoid MacrocyclesScholl reactionπ- extensionstrain energymacrocycles increasesphenylene ring systemmacrocyclic structurecontextSE
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