Page 1163 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 12.20. Baeyer-Villiger Oxidation 1139

1 a O H SO 5 O SECTION 12.5
2
C H O Oxidation of Ketones
4 9
57% and Aldehydes
C H
4 9
2 b CH CO H O
3
3
O
O
85%
3 c
O CH CO H O 88%
3
3
O
4 d
Cl CH CO H Cl
3
3
OCCH 3
Cl COCH 3 Cl
O 80%
5 e O CO 2 – O O (CH ) CH 3
2 3
(CH ) CH 3 Mg ++
2 3
CO 3 –
92%
6 f O
O
O
CF CO H
3
3
98%

7 g O O
CF CO H
3
3
CCH 3 OCCH 3
53%
h
8 (CH ) CO N CO CH 3
2
3 3 2 (CH ) CO N CO 2 CH 3
2
3 3
(CF CO) O
2
3
70% H O 2
2
Na HPO 4
2
CCH 3
O CCH 3 58%
2
O
a. T. H. Parliament, M. W. Parliament, and J. S. Fagerson, Chem. Ind., 1845 (1966).
b. P. S. Strarcher and B. Phillips, J. Am. Chem. Soc., 80, 4079 (1958).
c. J. Meinwald and E. Frauenglass, J. Am. Chem. Soc., 82, 5235 (1960).
d. K. B. Wiberg and R. W. Ubersax, J. Org. Chem., 37, 3827 (1972).
e. M. Hirano, S. Yakabe, A. Satoh, J. H. Clark, and T. Morimoto, Synth. Commun., 26,
4591 (1996); T. Mino, S. Masuda, M. Nishio, and M. Yamashita, J. Org. Chem., 62,
2633 (1997).
f. S. A. Monti and S.-S. Yuan, J. Org. Chem., 36, 3350 (1971).
g. W. D. Emmons and G. B. Lucas, J. Am. Chem. Soc., 77, 2287 (1955).
h. F. J. Sardina, M. H. Howard, M. Morningstar, and H. Rapoport, J. Org. Chem., 55,
5025 (1990).