Science of Synthesis

von Angerer, S., Science of Synthesis, (2005) 26, 61.

Sodium and calcium hypochlorite have also been used as oxidizing agents, though their scope is not well-established.[‌151‌,‌152‌] The reaction with sodium hypochlorite can be improved when the oxidation is performed in a two-phase system under phase-transfer catalysis.[‌153‌] More important are reactions of sodium hypochlorite which proceed via catalysts that undergo intermediary oxidation. Cyclic secondary alcohols are oxidized to the corresponding ketones in excellent yields using sodium hypochlorite in a two-phase system in the presence of tetrapropylammonium perruthenate.[‌154‌,‌155‌] A representative example is the oxidation of the pyranose ‌56‌ to the oxo derivative ‌57‌ (‌Scheme 35‌)

‌Meeeee 88‌ Meeeeeeee ee e Meeeeeeee Meeeeeeee Meeeeeee eeee Meeeee Meeeeeeeeeee ee eee Meeeeeee ee Meeeeeeeeeeeeeeeeee Meeeeeeeeeee[‌888‌]

M eeeeeeee eeeeeeee eee eeeeeeeeee ee eeeeeeee ee eeeeeee ‌88‌ ee eeeeee eeeeeeeeeeee ee eee 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee eeeeeee (MMMMM)[‌88‌] ee eee 8-eeeeeee eeeeeeee, eeeee eee eeeeeeeee ee eeee eeee eee eeeeeeeeeeeee eeeeeeeeeee eeeee.[‌888‌] Mee eeeeeeee ee eeeeeeeee eeeeeee ee eeeeeeeeee eee ee eeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeee ee eeeeeeeeeee ee eeeeeeeee ee eeeeeee eeee eeeeeeeeeeee (‌Meeeee 88‌). Meeee eeeeeee eeeeeeee eeeee eeee eeeeee eeee eeeeeeeee eeeeeeee eeeeeeeee eeeeeeeeee ee eeeeeee eeeeeeeee ‌88‌ (M8 = M) eee ee eeeeeeee.

‌Meeeee 88‌ Meeeeeee eee Meeeeeee Meeeeeeee ee eee 8,8,8,8-Meeeeeeeeeeeeeeeeeee-8-eeee-Meeeeeeee Meeeeeeee ee Meeeeeee[‌88‌]

Me eeeeeeeeeee eeeeeeee eee eeee eeee ee eeeeeeee ee eee 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee eeeeeee eeeeee ee e eeeeeee ee eeee ee eeeeeeeeee eeeeeeee.[‌88‌,‌888‌] Meee eeeeeeeeeee-eeeeeeeeeeeeee eeeeee eee ee eeeeeee eeee 8,8,8,8-eeeeeeeeeee-8-eeeeeeeeeeee-8-eeee eeeeeee ee eeeeeeeeeee eeeeeeee ee eeeee eeeeeee eee eee eeeeeeeee ee eeeeeeee eeee eeeeee eeeeeeeeeeee ee eeeeeeeee, ee eeeeeeeeeee ee eee eeeeee eeeeeeeeeeee eeeeeeeeee ee eeeee-8-ee eeee eeeee-8-eee (‌88‌) (‌Meeeee 88‌).[‌888‌] Meeeee eee eee ee eeeeeeee ee eeee(eeeeeeee eeeeee) ee eee eeeee eeeeeee eee eee eeeeeeeeeeeeeeeeeeee-8-eeee eeeeeee eeeeeee eeeeeeeeee ee eee ­eeeeeeee eeeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeee-8-eee ee Meeeeeeee eeee Meeeee Meeeeeeeeeee ee eee Meeeeeee ee 8,8,8,8-Meeeeeeeeeeeeeeeeeee-8-eeee Meeeeee ee Meeee Meeeeee[‌888‌]

eeee-Meeee eeeeeeeeeeee eee eeee ee eeee eee eee eeeeeeeee ee eeeeeeeee eeeeeeee eee eeeeeeee ee eeeeeeee.[‌888‌] Meeeeee eeeeeee eee eeeeeeee ee eeeeeeeee eeee eeee-eeeee eeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeeee ee eeee eeeeee.[‌888‌] Meeeee eeeeeeeeeeee eeeee eeee ee ee eeeeeeeeeee eeeeeee eee ee ee eeee eeeeeeee. Meeeeeeee, ee ee eeeeeeeee ee eeee ee eeeeeeeee e eeeeeeee ee eeeeeeee ee eeeeeeee eeeeee eeeeee eee eeeeeeeee eeeeeee ee ee eeeeeeee. Meee eeeeeee eeeeeeeeeeeeee eeeeeeee eeeeeeeee eeeeeee eeeeee eee eeeeee eeeeeee eeeeeeee eeeeeeeeee.[‌888‌]

Meeeeee ee eeeeeeeeeee, eeeeeeeee eeeeeeee eeee ee eeeeeeee ee eeeeeee (eee Meeeeee ‌88.8.8.8.8.8‌) eee ee eeee eeeeeeee eee eee eeeeeeeeee ee eeeeeeee eeee eeeeeeee eeeeeeeee, eee eeee eeeeeee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeee ee eee eeeeeeeee ee 8-(eeeeeeeeeeeee)eeeeeeeeeeeee (‌88‌) (‌Meeeee 88‌).[‌888‌] Meeee eeeee eeee eeeeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeee ee eee eeeeeeee ee eeeeeeee. Meeeeeeee eeee eeeeeee eee eeeeeeeee eeeeeee eeeeee eeeeeee eee eeeeeeeeeee eeeeeeee ee eeee eee eeeeeee eeeeeee.

‌Meeeee 88‌ Meeeeeeee Meeeeeeee ee Meeeeeeee Meeeeee Meeeee ee Meeeeeee eee Meeeeee, Meeeeeeeeeee, ee eee Meeeeeee ee Meeeeeeeeeeeeeeeeeee Meeeeeee[‌888‌]

Mee eeeeeeee eeeeeeeeee eeee eee eeeeeeee ee eeeeeeee eee ee eeeeeeeee eeee eeeee­eeeee­eeeeeeee eeeeeeeeeee ee eeee ee eee eeeeeee. Me eee eeeeeeee ee eeeeeeee eee 8,8-eeeeeeeeeeee[8.8.8]eeeeee ee eeeeeeeeeeee, ee eeeeeeee eeeeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeee.[‌888‌] Meee eeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeee eeeeeee eeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeeee ‌88‌ ee 8,8,8,8-Meeeeeeeeeeeeeeeeeee-8-eeee-Meeeeeeee Meeeeeeee eeee Meeeee Meeeeeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

M 88-eM eeeeeeee eeeee eeeeeeeeeeee ee 8°M eee eeeeeee eeee e eeee ee eee eeeeeee (88 eeee) ee MM8Me8 (8 eM), 8.888 M 8-eeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee ee MM8Me8 (8 eM), eee ee 8.8 M MMe (8.8 eM). Meee, ee 8.88 M MeMMe (88.8 eM) ee eM 8.8 eee eeeee eee eee eeeeeee eee eeeeeee ee 8888 eee. Me eee eee ee eee eeeeeeee, eee eeeeeee eeeee eee eeeeeeeee eee eeeee (MeMM8). Meeee eeeeeeeeeee ee eee eeeeeee, eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeeeeee; eeeee: 88–88%.

Meeeeeeee eeee Meeeee Meeeeeeeeeee ee eee Meeeeeee ee 8,8,8,8-Meeeeeeeeeeeeeeeeeee-8-eeee ee Meeee Meeeeee: Meeeeeeee ee Meeee-8-eee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

Meeeee eee eeeeeeeee MMMMM (88 ee, 88 μeee ee MMMMM eeeeeeeee ee eeeeeeeeeeeee) eee eeeeee ee eee eeeeeeee eeeeee. M eeee ee eeeee-8-ee (8.8 eeee) ee MM8Me8 (88 eM) eee ee 8.8 M MMe (8.8 eM) eeee eeee eeeee. Meeee eee eeeeeee eee eeee eeeeee ee 8°M, ee ee MeMMe eeee (88.8 eM, eeeeeee ee e eeeee eeeeeeeeeeeee ee 8.88 M eee eeeeeeee ee eee eeeeeeee ee MeMMM8 ee e eM ee 8.8) eee eeeee. Mee eeeeeee eee eeeeeeeeee eeeeee eee 88 eee. Meeee eeeeeeeeee, eee eeeeeee eeeee eee eeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eee eeeeeee eee eeeeeee ee eeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8); eeeee: 88%.

Meeeeeeeee eeee Meeeeeee: Meeeeeeee ee 8-(Meeeeeeeeeeee)eeeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeee ee e eeeeee eeeeeeee ee eee eeee, eeeeee eeeeeeeee, eeeee, eee eeee. Meeeee eeeeeee eeeeee eeeeee eee eeeeeee eeeee ee eeeeeee eeee eeee eee eeee.

MMMMMMM: Meeeeeeeeeeeeeeeeeee eeeeeeee ee e eeeeeeee eeeee eeeeeeeeee eee ee eee eee eeee eeeeeeee.

Meeeee M: M eeee ee Me8 ee MMMe8 (eeeeee ee eee eeee ee eee eeeeeeeeeee) eee eeeee eeeeeeee ee e eeeeeeeeee eeeeeee eeeeeeeeeeee eeeeeee ee 8-(eeeeeeeeeeeee)eeeeeeeeeeee eee MMMM ee MM8Me8 eee ee 8–8 M MeM8MM8 ee 8°M. Meeeeeee eee eeeeeeeee ee 8–8°M eeeee eee eeeeeee eeeee eee eeeeeeeeee eeeeeeeeeee ee ee eeee eeeeeeee eeeeeee eeeee ee eeeeeeee ee MMM eee ee MM ee eee eeeeeee eeeee.

Meeeee M: M eeee ee Me8 ee MM8Me8 eee eeeee eeeeeeee ee e eeeeeeeeee eeeeeee eeeeeeeeeeeee eeeeeee ee 8-(eeeeeeeeeeeee)eeeeeeeeeeee eee MMMM ee MM8Me8 (8–88 eM·eeee−8 ee eeeeeee eeeeeeeee ee eee eeeeeeeeee ee eee eeeeeeeee) eee 8% ee MeMMM8 ee 8°M. Meeeeeee eee eeeeeeeee ee 8–8°M eeeee ee eeee eeeeeeee eeeeeee eeeee ee eeeeeeee ee MMM eee/ee MM ee eee eeeeeee eeeee.

Mee eeeeeee eeeee ee eee eeeeee (eeee Meeeee M ee Meeeee M) eee eeeeeeeee eeeeeeeeee eeeee eeeeeee eeeeeeee (88 Meee). Mee eeeeeeeee eeeeeee eeeee eee eeeeeeeee eeee eeeeee/Me8M (8:8). Mee eeeeeee eeee eee eeeeee eeee 8% MMe (8–8 × 88 eM), 8% MeMMM8 (8 × 88 eM), eee M8M (8 × 88 eM). Mee eeeeeee eeeee eee eeeee (MeMM8) eee eee eeeeeee eeeeeeee ee eeeeeee eeeeeeeeeee ee eee eeeeeeee eeeee eeeeeee eeeeeeee. Me eeeeeeeee, eeeeee ee MMMM eee eeeeeeeeee eeee eeeeeee ee eeeeeeeeeeeeee; eeeee (Meeeee M): 88%; eeeee (Meeeee M): 88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.