3 research outputs found
Discovery of Deep-Seated Skeletal Rearrangements in the Photocyclizations of Some <i>tert</i>-Butyl-Substituted 1,2-Diarylethylenes
The
in-solution oxidative photocyclization of stilbenes to phenanthrenes
is a well-known and synthetically valuable reaction. We report here
our discovery that the oxidative photocyclization of several <i>tert-</i>butyl-substituted 1-styrylphenanthrenes resulted not
only in the expected formation of <i>tert-</i>butyl-substituted
picenes but also in the previously unknown rearrangement leading to
the formation of <i>tert-</i>butyl-substituted pentahelicenes
Phenyl Groups versus <i>tert</i>-Butyl Groups as Solubilizing Substituents for Some [5]Phenacenes and [7]Phenacenes
In recent years, we have used the photocyclizations of
diarylethylenes to synthesize a number of [<i>n</i>]Âphenacenes
in the hope that they might be useful as the bridging groups for electron
transfer processes in donor–bridge–acceptor molecules.
Because [<i>n</i>]Âphenacenes with <i>n</i> >
5 are very insoluble, their synthesis and characterization has required
the attachment of solubilizing substituents such as <i>tert</i>-butyl. The studies of Pascal and co-workers of some large polynuclear
aromatic compounds having multiple phenyl substituents prompted us
to explore the use of phenyls as alternative solubilizing groups for
[<i>n</i>]Âphenacenes. Although phenyl groups turned out
to provide significantly less solubilization than <i>tert</i>-butyl groups in these compounds, we found some interesting structural
comparisons of the phenyl-substituted and <i>tert</i>-butyl-substituted
[<i>n</i>]Âphenacenes
Phenyl Groups versus <i>tert</i>-Butyl Groups as Solubilizing Substituents for Some [5]Phenacenes and [7]Phenacenes
In recent years, we have used the photocyclizations of
diarylethylenes to synthesize a number of [<i>n</i>]Âphenacenes
in the hope that they might be useful as the bridging groups for electron
transfer processes in donor–bridge–acceptor molecules.
Because [<i>n</i>]Âphenacenes with <i>n</i> >
5 are very insoluble, their synthesis and characterization has required
the attachment of solubilizing substituents such as <i>tert</i>-butyl. The studies of Pascal and co-workers of some large polynuclear
aromatic compounds having multiple phenyl substituents prompted us
to explore the use of phenyls as alternative solubilizing groups for
[<i>n</i>]Âphenacenes. Although phenyl groups turned out
to provide significantly less solubilization than <i>tert</i>-butyl groups in these compounds, we found some interesting structural
comparisons of the phenyl-substituted and <i>tert</i>-butyl-substituted
[<i>n</i>]Âphenacenes