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36.1.1.1.10 Variation 10: Oxidation with Methyltrioxorhenium(VII)

DOI: 10.1055/sos-SD-036-00003

Porter, M. J., Science of Synthesis, (2008) 36, 32.

Catalytic methyltrioxorhenium(VII) (MTO), in conjunction with excess hydrogen peroxide (to generate methyloxodiperoxyrhenium in situ), oxidizes tertiary C—H bonds to the corresponding alcohols in variable yield and with retention of configuration (‌Table 8‌).[‌88‌] Polymer-supported variants of the catalyst have also been developed for use in conventional solvents[‌89‌] or ionic liquids.[‌90‌] Although this modification simplifies the workup, the isolated yields tend to be somewhat lower.

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Meeeeeee ­Meeeeeee Meeeeeeeeee Meeeeee Meeee (%) Mee
M8M8 (88 eeeee), MMM (88 eee%), e-MeMM, 88°M, 88 e 88 [‌88‌]
M8M8 (88 eeeee), MMM (88 eee%), e-MeMM, 88°M, 88 e 88 [‌88‌]
M8M8 (88 eeeee), MMM (88 eee%), e-MeMM, 88°M, 88 e 88 [‌88‌]
M8M8 (88 eeeee), MMM (88 eee%), MeMM, 88°M, 88 e 88 [‌88‌]
Me8MM M8M8 (88 eeeee), MMM (88 eee%), MeMM, 88°M, 88 e Me8MMM 88 [‌88‌]

e MMM = eeeeeeeeeeeeeeeeeee(MMM).

References

[88] Meeeee, M. M.; Meeeee, M.; Meee, M.; Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888.
[89] Meeeeeeee, M.; Meeeeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 88888.
[90] Meeeeeeee, M.; Meeeeeeeeee, M.; Me Meeeeee, M.; Meee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888.

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