Page 579 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 6.12. [3,3]-Sigmatropic Rearrangements 553

a
1 Cope rearrangement SECTION 6.4
[3,3]-Sigmatropic
Rearrangements

b
2 Oxy-Cope rearrangement
HO HO O

c
3 Anionic oxy-Cope rearrangement
– –
O O O
H +
d
4 Claisen rearrangement of allyl vinyl ethers
O O

d
5 Claisen rearrangement of allyl phenyl ethers
O O OH

e
6 Ortho ester Claisen rearrangement
OR OR
RO OR
O –ROH O O

f
7 Ireland-Claisen rearrangement of O-allyl-O ′-trimethylsilyl ketene acetals
OSiMe 3 OSiMe 3
O O

g
8 Ester enolate Claisen rearrangement
O – O –
O O

h
9 Claisen rearrangement of O-allyl-N,N-dialkyl ketene aminals
NR 2 NR 2
O O

(Continued)