Science of Synthesis

Suffert, J., Science of Synthesis, (2005) 26, 939.

Hydroxy(mesyloxy)iodobenzene oxidizes aliphatic ketones and affords the mesyloxylated derivatives ‌221‌.[‌191‌] Yields are good, and the reactions proceed under reflux in acetonitrile; they may involve an enolic intermediate such as ‌220‌. Although the α-mesyloxylation of 1-cyclopropylethanone with this reagent is regiospecific and affords ‌222‌ in ~100% yield, such precision is not generally observed. Thus, when butan-2-one is oxidized in acetonitrile a 5:4 mixture of the isomers ‌223‌ and ‌224‌ is obtained (‌Scheme 101‌).[‌191‌]

‌Meeeee 888‌ α-Meeeeeeeeeeeee ee Meeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee-8-eeeeeeee Meeeeeeeeeeeeeee (‌888‌):[‌888‌]

8-Meeeeeeeeeeeeeeeeee (8.888 e, 88 eeee) ee MeMM (8 eM) eee eeeee ee MeM(MM)MMe (8.88 e, 88.8 eeee) ee MeMM (88 eM), eee eee eeeeeee eee eeeeeee eee eeeeeeee eee 88 eee. Me eee eeee eeeeeeeeeeee ee eeeee ee eee, eeeee eee eeeeeeeeeee ee Me8M (88 eM), eee eeeeee eeee M8M (8 × 88 eM), eeeee (MeMM8), eee eeeeeeeeeeee. Meeee eeeeee eeeeeeeeeeeeee ee eee eeeeeee [eeeeee eee (88 e), eeeeeee (888 eM, ee eeeeee eeeeeeeeeee) eee eeee MM8Me8 (888 eM)] eeee e eeee eeeeeeee-eeeeee eeeeee; eeeee: 8.88 e (~888%); ee 88–88°M (Me8M).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e, 8888.