investigate cleavage
DESCRIPTION
Investigate cleavage. 1) WO 4 2- , H 2 O 2. 100 o C, 10 hrs. 85% yield. O=COCH 3. C. 1) WO 4 2- , H 2 O 2 , 100 o C. 2) H + , H 2 O, 100 o C. 10% yield. H 2 O, H 3 PO 4 , 90 o C. 8%. 13%. 1) HCOOH, H 2 O 2 , 90 o C. 2) NaOH, H 2 O, 100 o C. 50% yield. - PowerPoint PPT PresentationTRANSCRIPT
Investigate cleavageInvestigate cleavage
H3COOC
O
OH
OH
COOH
OMe
OMe
COOH
O
O
COOH
O
O
HOOC COOH
HOOC CH3
+100oC
WO42-, H2O2, PTC
H3COOC
O
COOCH3
1) WO42-, H2O2 100oC, 10 hrs
85% yield
C O
O=COCH3
H3COOC
O
1) WO42-, H2O2, 100oC
HOOC COOH
2) H+, H2O, 100oC
10% yield
1122334455667788991010111112121313
H3COOC
O
H2O, H3PO4 , 90oC
H3COOC
COOCH3
HO
O
O
H3COOC
OH
H3COOC
COOCH3
HO
O
OH
COOCH3
HO
OH
COOH
HO
OH
8% 13%
COOH
OH
OH
COOH
1) HCOOH, H2O2, 90oC 2) NaOH, H2O, 100oC
50% yield
1) WO42-, H2O2, 100oC
HOOC COOH
1% yield
COOH
OH
OH
Ac2O, H3PO4, 100oC
39% yield
COOH
OH
OH
OH
C
O
O
OAc
C
OAc
O
OAc
KOH, DMSO, MeI 40oC
59% yield
COOH
OH
OH
COOMe
OMe
OMe
1) WO42-, H2O2, 100oC
HOOC COOH
COOMe
OMe
OMe
OH
C
O
O
OAc
C
OAc
O
OAc
X
Investigate cleavageInvestigate cleavage
H3COOC
O
OH
OH
COOH
OMe
OMe
COOH
O
O
COOH
O
O
HOOC COOH
HOOC CH3
+100oC
WO42-, H2O2, PTC
10%
1%
O
C O
OH
OH
OH
COOH
n-1
COOH
WO42-, 5eq H2O2 100oC, 24 hrs
70% yield,
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
-2E+07
0
2E+07
4E+07
6E+07
8E+07
1E+08
1E+08
1E+08
2E+08
2E+08
2E+08
2E+08
2E+08
3E+08
3E+08
3E+08
3E+08May12-2009Chemist Hoong Sing Soissh1-9 productPROTON.w CDCl3 u SSH 6
1.0
0
5.6
30.5
81.4
4
0.9
9
0.0
3
0.1
0
0.1
0
0.0
3
COOH
WO42-, 5eq H2O2 80oC, 24 hrs
COOH
WO42-, 5eq H2O2 60oC, 24 hrsX
0.51.01.52.02.53.03.54.04.55.05.5f1 (ppm)
-2E+07
0
2E+07
4E+07
6E+07
8E+07
1E+08
1E+08
1E+08
2E+08
2E+08
2E+08
2E+08
2E+08
3E+08
3E+08
3E+08
3E+08
3E+08
4E+08
4E+08
4E+08
COOH
WO42-, 1.5 eq H2O2 100oC, 24 hrs
COOH
WO42-, 2.5 H2O2 100oC, 24 hrs
H3COOC
O
Glycerol, BF3.Et2O, 65oC
COOCH3
O
O
H3COOC
O
COOCH3
OHNa
OH
OH
H3COOC
O
Glycerol, BF3.Et2O, 65oC
CH2OC
CHOC
O
CH2 CH7 CH
CH2 CH7 CH CH2 CH37
CH2OC
O
CH2 CH7 CH
O
O
O
O
CH2 CH3CH CH
O
4
CH2 CH3CH CH
O
4
Glycerol, BF3.Et2O, 65oC
Sticky Rubber like polymer