ChemInform Abstract: A COMPARATIVE STUDY OF JONES′S, COLLIN′S AND COREY′S REAGENTS IN THE CHROMIUM(VI) OXIDATION OF AN EPIMERIC PAIR OF ALLYLIC ALCOHOLS IN THE BENZO-FUSED NORBORNEN-5-OL SERIES

1978 ◽  
Vol 9 (32) ◽  
Author(s):  
R. N. WARRENER ◽  
T. S. LEE ◽  
R. A. RUSSELL ◽  
M. N. PADDON-ROW
Keyword(s):  
Comparative Study ◽  
Allylic Alcohols ◽  
Chromium Vi

A comparative study of Jones's, Collins's and Corey's reagents in the chromium(VI) oxidation of an epimeric pair of allylic alcohols in the benzo-fused Norbornen-5-ol series

1978 ◽  
Vol 31 (5) ◽  
pp. 1113 ◽  
Author(s):  
RN Warrener ◽  
TS Lee ◽  
RA Russell ◽  
MN Paddon-Row
Keyword(s):  
Comparative Study ◽  
Manganese Dioxide ◽  
Secondary Alcohol ◽  
Quantitative Yield ◽  
Current Understanding ◽  
Allylic Alcohols ◽  
Unsaturated Ketone ◽  
Oxidizing Agents ◽  
Chromium Vi ◽  
Ketone Formation

A comparison has been made between a series of chromium(VI) oxidizing agents, as well as manganese dioxide, a bicyclic allylic secondary alcohol, the exo-ol (7), being the substrate. Jones's, Collins's and Corey's reagents gave, in each case, a mixture of products: the main reactions were epoxidation to yield (8) and (9), normal ketone formation (10), and ring-fragmentation to form the indanol (11) and the indanone (12). All reagents yielded substantial amounts of epoxide, which is rare for Collins's reagent, and unprecedented for Corey's reagent, and varying amounts (13-30 %) of ketone, while Jones's reagent alone gave significant ring-opened products. A dramatic change in product composition was observed with the epimeric endo-alcohol (13), where Jones's reagent (only one studied) yielded the related α,β,-unsaturated ketone (10) in essentially quantitative yield. A discussion of these results is presented in terms of the current understanding of the mechanism of chromium oxidations.

Comparative study of oxidation by chromium(V) and chromium(VI)

1996 ◽  
pp. 1607 ◽  
Author(s):  
Sandra Signorella ◽  
Marcela Rizzotto ◽  
Ver�nica Daier ◽  
Mar�a I. Frascaroli ◽  
Claudia Palopoli ◽  
...  
Keyword(s):  
Comparative Study ◽  
Chromium Vi

Comparative Study of Chromium(V) and Chromium(VI) Oxidation of Dialkyl Sulfides

Tetrahedron ◽  
2000 ◽  
Vol 56 (32) ◽  
pp. 5885-5892 ◽  
Author(s):  
Tharumeya Kuppusamy Ganesan ◽  
Seenivasan Rajagopal ◽  
Jesuraja Bosco Bharathy
Keyword(s):  
Comparative Study ◽  
Chromium Vi ◽  
Dialkyl Sulfides
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