Uploaded May 2022 | Updated September 2026, 1 week ago

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In this episode, I discuss 1,2-shifts of ketols and related compounds, in reactions such as Criegee rearrangement, alpha ketol rearrangement, and benzilic acid rearrangement!

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Links to articles discussed in this episode:

3rd practice problem - doi.org/10.1021/jo9603338
OG Büchner–Curtius–Schlotterbeck - doi.org/10.1002/cber.188501802118
OG Criegee - doi.org/10.1002/cber.19450770912
1st Criegee - doi.org/10.1021/ja01163a072
2nd/3rd Criegee - doi.org/10.1021/jo00097a006
orthoester - doi.org/10.3998/ark.5550190.0006.412
Criegee review - doi.org/10.3762/bjoc.12.162
(maybe) OG alpha-ketol - doi.org/10.1002/prac.18860340101
1st ketol - doi.org/10.1016/0039-128X(91)90068-7
2nd ketol - doi.org/10.1016/S0040-4039(01)94374-6
3rd ketol - doi.org/10.1039/C9GC00336C
4th ketol - doi.org/10.3987/COM-98-S(H)63
amazing ketol review - doi.org/10.1002/0471264180.or062.03
OG Benzilic - doi.org/10.1002/jlac.18380250102
1st benzilic - doi.org/10.1021/jm00368a009
2nd benzilic - doi.org/10.1021/jacs.5b01517
3rd benzilic - doi.org/10.1039/C2OB26737C
4th benzilic - doi.org/10.1039/C3RA42929F
1st practice - doi.org/10.1016/S0040-4039(98)01465-8
2nd practice - doi.org/10.1021/jo00302a027
3rd practice - doi.org/10.1016/S0040-4039(01)02368-1
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