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26.1.2.2.2 Variation 2: Using Permanganate and Periodate Reagents

DOI: 10.1055/sos-SD-026-00062

Balaban, T. S., Science of Synthesis, (2005) 26, 134.

Internal and terminal alkenes[‌62‌,‌63‌] can be almost quantitatively cleaved by a combination of permanganate oxidation with periodate diol cleavage. This method has been applied to the oxidation of isopropylidene groups, e.g. in terpenes. A synthetically useful example is the oxidation of 5,5-dimethyl-2-methylenebicyclo[2.1.1]hexane to 5,5-dimeth­ylbicyclo[2.1.1]hexan-2-one (‌Scheme 12‌).[‌64‌]

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References

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[64] Meeeeeee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888.
[65] Meeeeeee, M. M. M.; Meee, M. M.; Meeeee, M. M.; Meeeeeeee, M., M. Mee. Meee., (8888) 88, 8888.

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