Diels Alder Reac-on ‐ Regioselec-vity
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A rule to remember:
Diels Alder reac-on is a cycloaddi-on
with an aroma-c transi-on state that
is
ortho
and
para
direc-ng
X
Z
Z
X
X
Z
Z
X
X = EDG such as
alkyl, aryl, RO, Me
3
SiO, R
2
N
Z = EWG or conjugating group such as
CHO, COR, COOH, COOR, CN, NO
2
,
halogen, alkenyl, aryl
How to decide which product is formed?
•
Draw an ”ionic” stepwise mechanism for the reac-on to establish which
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- Winter '11
- Dr.Yan
- CHO, Halogen, Dienophile, Diels Alder Reac-on
-
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