Wolff rearrangement of alpha-diazoketones using in situ generated silver nanoclusters as electron mediators.
[reaction: see text] We report Wolff rearrangement of alpha-diazoketones by in situ generated silver nanoclusters (Ag(n)(), 2-4 nm) from silver(I) oxide (Ag(2)O) involving a nonclassical electron-transfer process. Our results show that Ag(n)()(+)/Ag(n)()(0) redox couple allows the initial removal of an electron from alpha-diazoketone and its back-donation after chemical reaction(s). Controlled potential coulometry (CPC) of various alpha-diazoketones results in the realization of Wolff-rearranged carboxylic acids in excellent yields.
Sudrik
Surendra G
SG
Division of Organic Chemistry Technology, Physical and Materials Chemistry Division, and Chemical Engineering & Process Development Division, National Chemical Laboratory, Pune-411008, India.
Sharma
Jadab
J
Chavan
Vilas B
VB
Chaki
Nirmalya K
NK
Sonawane
Harikisan R
HR
Vijayamohanan
Kunjukrishna P
KP