π‑Extension of Strained Benzenoid Macrocycles
Using the Scholl Reaction
Posted on 2018-10-19 - 23:55
A 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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Saha, Nirob
K.; Mitra, Nirmal K.; Johnson, Kara F.; Merner, Bradley L. (2018). π‑Extension of Strained Benzenoid Macrocycles
Using the Scholl Reaction. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b02979
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AUTHORS (4)
NS
Nirob
K. Saha
NM
Nirmal K. Mitra
KJ
Kara F. Johnson
BM
Bradley L. Merner
KEYWORDS
terphenyl-containing macrocyclesseriesScholl-based cyclodehydrogenation reactionregioselectively brominatedparaScholl Reactionarylatedalkyloxybenzenoid compoundshydrocarbon systemspolycyclicterphenyl unitExtensionStrained Benzenoid MacrocyclesScholl reactionπ- extensionstrain energymacrocycles increasesphenylene ring systemmacrocyclic structurecontextSE