Carbanion rearrangement studies on selected N-acyl-isoquinoline
and -quinoline Reissert compounds have shown that
alternative intramolecular rearrangements can compete successfully
with the normal 1,2-acyl-migration. The observations have been
rationalised mechanistically and their potential value in
synthesis demonstrated. In particular the formation of a
1-benzoyl-8-hydroxyisoquinoline derivative has been effected
from carbanion rearrangement of the corresponding 8-benzoyloxy
Reissert compound. N-Crotonoylisoquinoline Reissert compound
carbanion and analogous structures have been shown to undergo
a complex reaction in which Michael type attack competes with
the normal migration. [Continues.
