Page 1095 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 12.3. Oxidation of Alcohols Using Dimethyl Sulfoxide 1071

1 a CH 3 CH 3 SECTION 12.1
C DMSO
H 3 H C Oxidation of Alcohols to
CH OH 3 CH O Aldehydes, Ketones,
2
H C DCCI H C or Carboxylic Acids
3
3
84%
2 b CH
CH 3 CH 3 CH
H C 2 H C 2
3
CH 3 DMSO 3 CH 3
OH OH
SO 3
3 c OH O 44%
CH 3 DMSO CH 3
N C CH OH (CH CO) O N C CH O
2
H 3 2 H
4 d CH 3 CH 3 60%
) CO CH ) CO CH
(CH 2 6 2 3 (CH 2 6 2 3
CH OH DMSO CH O
ON 2 ON
PhSCH 2 PhSCH 2
OTHP N C NCH 2 CH N + OTHP
2
CH 3
5 e 98%
DMSO
(CH ) CHCH CHCH CHCH OH (CH ) CHCH CHCH CHCH O
2
3 2
3 2
ClCOCOCl 93%
6 f CO C(CH )
CH 3 2 3 3 DMSO, CH CO 2 C(CH )
3 3
3
CH 3 N ClCOCOCl CH N
CH OH 3 CH O
2
O (i-C H ) NC H O 99%
2 5
3 7 2
CN
7 g CN
OH CH 3 DMSO
O O CH 3
CHCH CH 3 O
H O (CF 3 CO) O CHC CH 3
2
8 h OCH 3 H O 90%
H H OH DMSO, H H OCH 3
P 2 O 5 O
CH 3 CH CH CHCH CO CH 3 CH CCH CO CH
2
2
2
2
Et N CH 3 CH 2 2 2 2 3
3
85%
a. J. G. Moffat, Org. Synth., 47, 25 (1967).
b. J. A. Marshall and G. M. Cohen, J. Org. Chem., 36, 877 (1971).
c. E. Houghton and J. E. Saxton, J. Chem. Soc. C, 595 (1969).
d. N. Finch, L. D. Veccia, J. J. Fitt, R. Stephani, and I. Vlatta, J. Org. Chem., 38, 4412 (1973).
e. W. R. Roush, J. Am. Chem. Soc., 102, 1390 (1980).
f. A. Dondoni and D. Perrone, Synthesis, 527 (1997).
g. R. W. Franck and T. V. John, J. Org. Chem., 45, 1170 (1987).
h. D. F. Taber, J. C. Amedio, Jr., and K.-Y. Jung, J. Org. Chem., 52, 5621 (1987).