ORGANIC OXOAMMONIUM SALTS .3. A NEW CONVENIENT METHOD FOR THE OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES

被引:190
作者
MA, Z [1 ]
BOBBITT, JM [1 ]
机构
[1] UNIV CONNECTICUT, DEPT CHEM, STORRS, CT 06269 USA
关键词
D O I
10.1021/jo00021a027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the selective oxidation of alcohols using organic oxoammonium salts generated by acid-promoted disproportionation of nitroxides in solution has been developed. Major advantages are high yields, ease of product isolation, and a high degree of selectivity in the presence of other functional groups.
引用
收藏
页码:6110 / 6114
页数:5
相关论文
共 42 条
[31]  
Rozantsev EG., 1971, B ACAD SCI USSR CH, V20, P768, DOI 10.1007/bf00853921
[32]  
Russell A, 1943, ORG SYNTH, V23, P78
[33]   MECHANISM OF THE OXIDATION OF ALCOHOLS BY 2,2,6,6-TETRAMETHYLPIPERIDINE NITROSONIUM CATION [J].
SEMMELHACK, MF ;
SCHMID, CR ;
CORTES, DA .
TETRAHEDRON LETTERS, 1986, 27 (10) :1119-1122
[34]   SELECTIVE OXIDATION OF PRIMARY HYDROXY-GROUPS IN PRIMARY-SECONDARY DIOLS [J].
SIEDLECKA, R ;
SKARZEWSKI, J ;
MLOCHOWSKI, J .
TETRAHEDRON LETTERS, 1990, 31 (15) :2177-2180
[35]   CATALYTIC DEHYDROGENATION OF PRIMARY AND SECONDARY ALCOHOLS WITH PLATINUM AND OXYGEN - SELECTIVE DEHYDROGENATION IN THE STEROID SERIES [J].
SNEEDEN, RPA ;
TURNER, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (01) :190-191
[36]  
STEPHEN H, 1925, J CHEM SOC, P1875
[37]  
Tidwell T.T., 1990, ORG REACTIONS, V39, P297, DOI DOI 10.1002/0471264180.OR039.03
[38]   STUDIES OF STABLE FREE RADICALS .20. NITRONYL NITROXIDE MONORADICALS AND BIRADICALS AS POSSIBLE SMALL MOLECULE SPIN LABELS [J].
ULLMAN, EF ;
OSIECKI, JH ;
BOOCOCK, DGB ;
DARCY, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) :7049-+
[39]  
YAMAGUCHI M, 1988, MAKROMOL CHEM-RAPID, V9, P203
[40]   NEW SELECTIVE OXIDATION OF ALCOHOLS CONTAINING ESTER GROUP WITH AN OXOAMINIUM SALT [J].
YAMAGUCHI, M ;
TAKATA, T ;
ENDO, T .
TETRAHEDRON LETTERS, 1988, 29 (44) :5671-5672