The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(8), С. 5304 - 5313
Опубликована: Апрель 9, 2024
Most
of
the
known
rearrangement
reactions
donor–acceptor
cyclopropanes
(DACs)
involve
migration
cationic
carbon
atom
to
anionic
or
heteroatoms
in
1,3-
1,4-positions.
In
present
work,
we
observed
that
spiro
DACs
based
on
1,3-indanedione
1-indanone
moiety
undergo
intramolecular
1,2-aroyl
when
treated
with
titanium(IV)
chloride
afford
1,4-naphthoquinones
and
α-naphthols
readily.
The
take
place
through
formation
putative
1,3-dipolar
intermediates,
followed
by
cleavage
aroyl
group
adjacent
ring-expansion
products.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(31), С. 6312 - 6316
Опубликована: Янв. 1, 2023
A
series
of
indolylthio-functionalized
ketones
were
constructed
via
a
ring-opening
reaction,
and
the
linear
could
be
further
transformed
into
dihydro-2
H
-thiepino[2,3-
b
]indoles.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(33)
Опубликована: Июнь 13, 2023
A
ligand-controlled
regiodivergence
in
Ni-catalyzed
rearrangement
of
vinylcyclopropanes
to
1,4-
or
1,5-disubstituted
cyclopentenes
is
reported.
The
cyclopentene
selectively
obtained
depending
on
the
choice
ligands.
Detailed
kinetic
studies
and
density
functional
theory
calculations
catalytic
cycle
revealed
that
product
selectivity
determined
at
reductive
elimination
step
from
six-membered
η1
-allyl
intermediate.
Chemical Communications,
Год журнала:
2023,
Номер
59(53), С. 8270 - 8273
Опубликована: Янв. 1, 2023
Efficient
annulation
of
in
situ
formed
azaoxyallyl
cations
using
a
base
has
been
accomplished
with
diaziridines
to
provide
1,2,4-triazines
at
room
temperature.
The
substrate
scope,
scale
up,
functional
group
tolerance
and
transition-metal
free
reaction
conditions
are
the
important
practical
features.
Russian Chemical Reviews,
Год журнала:
2024,
Номер
93(3), С. RCR5111 - RCR5111
Опубликована: Март 1, 2024
The
strained
structure
of
cyclopropanes
serves
as
a
kind
trigger
for
variety
chemical
transformations.
Among
others,
processes
involving
conjugated
unsaturated
systems
are
particular
interest.
bonds
characterized
by
the
possibility
flexibly
varying
their
reactivity
up
to
full
involvement
in
This
review
is
first
consider
options
implementing
idea
combining
strain
energy
and
synthetic
capacity
within
single
concept.
A
detailed
analysis
activated
numerous
carbodiene
heterodiene
presented.<br>
bibliography
includes
289
references.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(8), С. 5304 - 5313
Опубликована: Апрель 9, 2024
Most
of
the
known
rearrangement
reactions
donor–acceptor
cyclopropanes
(DACs)
involve
migration
cationic
carbon
atom
to
anionic
or
heteroatoms
in
1,3-
1,4-positions.
In
present
work,
we
observed
that
spiro
DACs
based
on
1,3-indanedione
1-indanone
moiety
undergo
intramolecular
1,2-aroyl
when
treated
with
titanium(IV)
chloride
afford
1,4-naphthoquinones
and
α-naphthols
readily.
The
take
place
through
formation
putative
1,3-dipolar
intermediates,
followed
by
cleavage
aroyl
group
adjacent
ring-expansion
products.
