Stevens rearrangement

Schematic representation of the Stevens rearrangement.
Mechanism of the Stevens rearrangement
Mechanism of the Stevens rearrangement
Original publication
Review
Sample reactions
intermediate structure
NaH
THF
50 - 55 °C, 2 d, 67%
intermediate structure
intermediate structure
KOt-Bu
THF
RT, 12 h, 75%
intermediate structure
intermediate structure
Cu(acac)2
PhMe
Reflux, 2.5 h, 82%
"The product is a 95:5 mixture of diastereomers at C-5 (major shown). 88:12 e.r."
intermediate structure