Illustrated Glossary of Organic Chemistry
Simmons-Smith reaction:
A
name reaction
in which a
carbenoid
adds
to an
alkene
or
alkyne
to form a
cyclopropane
.
+
Diiodo
methane
Organozinc
carbenoid
Cyclohexene
Bicyclo
[4.1.0]
heptane
This Simmons-Smith reaction begins with the
halogen-metal exchange
between diiodo
methane
(
methylene
iodide) and zinc (in a zinc/copper alloy) to produce a
reactive intermediate
organometallic
carbenoid
. This
carbenoid
then undergoes
cycloaddition
with the
pi bond
of
cyclohexene
(an
alkene
) to produce the
cyclopropane
ring of
bicyclo
[4.1.0]
heptane
.
Related terms:
Bicyclic
,
syn addition
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