Selective oxidation of 1,2-diols by electrochemical method using organotin compound and bromide ion as mediators

A new electrochemical method for a selective oxidation of 1,2-diols to keto alcohols was explored. The method used dibutyltin oxide and bromide ion as mediators, and the oxidation was found to proceed effectively at 0°C under neutral conditions. Under these reaction conditions, 1,2-cyclohexanediol w...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 7; pp. 651 - 654
Main Authors Maki, Toshihide, Fukae, Kazuhiro, Harasawa, Hitomi, Ohishi, Takahiro, Matsumura, Yoshihiro, Onomura, Osamu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 12.02.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUGARS
ORGANIC-SYNTHESIS
Online AccessGet full text

Cover

More Information
Summary:A new electrochemical method for a selective oxidation of 1,2-diols to keto alcohols was explored. The method used dibutyltin oxide and bromide ion as mediators, and the oxidation was found to proceed effectively at 0°C under neutral conditions. Under these reaction conditions, 1,2-cyclohexanediol was selectively oxidized even in the presence of primary and secondary alcohols. Selective oxidation of cis-1,2-cyclohexanediol 1 was achieved even in the presence of primary and secondary alcohols to keto alcohol 2 by electrochemical method using dibutyltin oxide and bromide ion as mediators.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10709-2