Inorg. Chem. 1991, 30, 2582-2584 Table I. ComDetitive Ewxidation of a-Methvlstvrene and Norbornvlene with Peracids Catalyzed by Iron(II1)
catalyst
run 1 2 3 4 5 6 7 8 9
IO 11 12 13 14 15 16 17 I8 19
none
none FeTMP(C1) FeTMP(0H) FeTMP(0H) FeTDMPP(C1) FeTDMPP(0H) FeTDCPP(C1) FeTDCPP(0H) FeTDCPP(0H) FeTPFPP(C1) FeTPFPP(C1) none
none FeTMP(C1) FeTMP(0H) FeTDMPP(C1) FeTDCPP(C1) FeTDCPP(0H)
oxidant m-CPBA m-CPBA m-CPBA
m-CPBA m-CPBA m-CPBA m-CPBA m-CPBA m-CPBA m-CPBA m-CPBA m-CPBA o-CPBA o-CPBA 0-CPBA o-CPBA o-CPBA
0-CPBA o-CPBA
solvent CHzC12 toluene CHzC12
O C
c
toluene
c -78 -78 -78 -78 -78 -78 -78 -78 -78 -78
CHZCIZ
C
toluene
c -78 -78 -78 -78 -78
CHlC12 toluene
CH2CI2 toluene
CH2CIz CH2CIz toluene
CH2ClZ
CHZCIZ toluene
CHZCIZ CHZCIZ toluene
76 yield 76 62 63 65 65 98 47 63 72 44 98 42 93 96 53 51 47 96 52
temp,
selectivity"
(norbornylene oxide (endo %)/
ratio of selectivity in
a-methylstyrcne oxide)*
toluene/CH2CI2
100 (0):30 100 (0):42 100 (4):9 100 (6):lO I 0 0 (2):74 100 (24):29 100 (
