Illustrated Glossary of Organic Chemistry
1,5-Hydrogen shift
(
[1,5-H] shift):
Migration of a hydrogen atom to an atom four
bonds
further away in a single
mechanism
step. A 1,5-H shift is an example of a
sigmatropic reaction
.
Decarboxylation
of this
beta-keto acid
occurs via a 1,5-H shift.
Related terms:
Carbocation rearrangement
,
McLafferty rearrangement
,
proton shuttle
,
proton bus
,
1,3-shift
,
1,3-H shift
,
1,2-shift
,
1,2-H shift
,
3,3-shift
,
malonic ester synthesis
,
acetoacetic ester synthesis
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