Science of Synthesis

Chataigner, I.; Harrison-Marchand, A.; Maddaluno, J., Science of Synthesis, (2005) 26, 1186.

A reasonable strategy for the synthesis of diketones is the oxidation of hydroxy ketones or diols. Among the oxidation methods commonly used are the Swern procedures,[‌528‌–‌530‌] Jones-type conditions [in the presence of chromium(VI) oxide],[‌530‌–‌539‌] and the use of the Dess–Martin reagent.[‌540‌,‌541‌]

Meee, e eeeeeee eeeeeeee ee 8,8-eeeeeeeeee eeeeeeeee ‌888‌ (‌Meeeee 888‌) eeeeeee e eee-eeee eeeeeeeee eeeee eeeeeeeee eeeee eeeeeeeeeeee ee e eeeeeeee eeeeeeee eeee ee eeeeeeee eeee eeeeeeeee ee eee eeeeeeeee eeeeeee eeeeee ‌888‌. Mee eeeeee eeee eee ee eeeeeeeee ee eeeeee ee eee eeeeeeee ee eee Meeee eeeeeeee (eee eeeeeeeee eeeeee eeeeeeee/eeeeeeee eeeeeeeee eeee eeeeeeeeeeeee[‌888‌] eee eee eeeee eeeeeeeee Meeee–Mee eeeeeeeeee eeee M-eeeeeeeeeeeeeeeee/eeeeeeee eeeeeee eeee eeeeeeeeeeeee[‌888‌]) ee ee Meeeeee eeeeeeeee eeee eeeeeeee(MM) eeeee/eeeeeeeeee.[‌888‌] Mee eeeee eeeeeee eeee eee 8,8-eeeeeeee ‌888‌ ee eeee eeeeee.

‌Meeeee 888‌ Meeeeeeee ee Meeeeee Meeeeee ee 8,8-Meeeeeeee[‌888‌,‌888‌]

Mee eeeeeeeee ee eeeeee β-eeeeeee eeeeeee ee eeeee eeeeee β-eeeeeeeee ‌888‌ (‌Meeeee 888‌) eeeeeeee eeeeeee eeeeeeeeeeeee ee eee eeeeeeee ee eee Meee–Meeeee eeeeeeeeeee.[‌888‌,‌888‌]

‌Meeeee 888‌ Meee–Meeeee Meeeeeeee ee e Meeeee β-Meeeeee Meeeee[‌888‌,‌888‌]

8,8-Meeeeeeee ‌888‌ (‌Meeeee 888‌) eee eeeeeeee eeeeeeee eeee eee eeeeeeeeeeeee 8-eeeeeee eeeeeee ee eeeeeeeee eeee eeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeee[‌888‌–‌888‌] ee eeeeee eeeeeeeeee ee eeeee.[‌888‌] 8,8-Meeeeeeee eee eeee ee eeeeeeeeeee ee eeeeeeeee eeeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeee eeeeeeeeeeee eeee 8-eeeeeeeeee M-eeeee ee eee ee-eeeeeee eeeee eeeeeeeeeeee eeeeeeeeee.[‌888‌]

‌Meeeee 888‌ Meeeeeeeee Meeeeeeeeeeeee Meeeeeeee ee e 8-Meeeeee Meeeee[‌888‌–‌888‌]

Meee eeeee eee eeeeeeee ee eeeeeeee eeeeeeeee, eee eee ee eeeeeeee eeeeee, eeee ee eee Meeee eeeeeee [eeeeeeee(MM) eeeee/eeeeeeee eeee], eeeee eeeeeeeee,[‌888‌–‌888‌] ee eeeeeeeeeee eee eeeeeeeee ‌888‌ (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeee Meeeeeeee ee 8,8-Meeee[‌888‌]

Meeeeee, Meeee eeeeeeeeee, eeeee eee eeeee ee ee eeee eeeeee, eee eeeeee eeeeeee eee eeeeee eeeeeeeeeeeeee eeeeeeeeee eeee ee eee 8,8-eeeeeeee ‌888‌ (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeee Meeeeeeee Meeeeeee ee e Meeeee Meeeeeeeeeeeee Meee[‌888‌]

Me eeee eeeeeeeee, eee eeeeeeee ee eeeeeeeeee ee eeeeeeeee ee eee 8,8-eeee eeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeee/eeeeeeee eeeeeeeee eeeeeee eee eeeeeeeeee eeeeeeeeeeeeeee. Meeeeee eeeee eee ee eeeeeeeeeee eeeeeee ee eeee eeeeee ee eeee eeeeeeeee. Meee eeeeeeeeeeeeee, eeeeee ee e eeee eeeeeee ee e eeeeeeeeeee, ee eeeeeeee ee Meeeeee ‌88.88.8.8.8.8‌.

Meeee eeeeeeeee eeeeeeee eeee ee eeeeee eeeeeeeeeeee,[‌888‌] eeeeeeeee(MM) eeeee,[‌888‌,‌888‌] ee eeeeeeeeeeeeeeeee[‌88‌] eee eeee eeeeeeeee ee eeeeeeeeeeee eeeeeee eeeeeee ee eeeee eeee eeeeeeeeee eeeeeee.

Mee eeeeeeeee ee eeeeee ee eeeeeee eeeee ee eeeeeeeee. Me eee eeeeeeeeee eeee ee eeeeee ee eeeeeeeee, eeee eeeeeeeeeeee eeeeeee eeee eeeeeee ee ee eeeeeeeeee eeeeeeeeeee (eeeeeeeeeeeeeeee ee eeeeee). Meeee eeeeeeeee eeeeeeeee eee eeeeeeeee ee Meeeeee ‌88.88.8.8.8.8‌.

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-eeeeeeeeeeeee-8,8-eeeee (‌888‌, M8 = Me; M8 = Me; M8 = M; M8 = Me) ee Meeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee eeee ee eeeeeee eeeeeeeee eeeeee eeeeeeee (8.888 eM, 8.88 eeee) ee MM8Me8 (8 eM) eee eeeeee ee –88°M eee e eeee ee eeeeeee eeeeeeeee MMMM (8.888 eM, 8.88 eeee) ee MM8Me8 (8 eM) eee eeeee eeeeeeee; eeeeeeee eee eeeeeeeee eee e eeeeeee 8 eee. M eeee ee eee β-eeeeeee eeeeee ‌888‌ (M8 = Me; M8 = Me; M8 = M; M8 = Me; 8.88 eeee) ee MM8Me8 (8 eM) eee eeeee eeeeeeee eeee 8 eee eee eee eeeeeeeee eeeeee eee eeeeeee eee 88 eee ee –88°M. Me8M (8.88 eM, 8.8 eeee) eee eeee eeeee eee eeeeeeee eee eeeeeeeeee eee ee eeeeeeeeee 8 eee ee –88°M. Mee eeeeeee eee eeeeee ee ee eee M8M (8 eM) eee eeeee. Mee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM) eee eee eeeeeee eeeeee eeee eeeeee eeee 8% ee MMe (88 eM), 8% ee Me8MM8 (88 eM), eee eeeee (88 eM), eeee eeeee (MeMM8). Mee eeeeeee eee eeeeeee ee eeeee eee eee eeeeeeee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee; eeeee: 8.888 e (88%).

8-Meeeee-8-eeeeeeeeeeeee-8,8-eeeee (‌888‌, M8 = Me; M8 = Me; M8 = M; M8 = Me) ee Meeeeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeee(MM) eeeee eeee eeeeeeeee eee eeeeeeeeeee eeeeee eee ee eeeeeeeeee ee e eeeee eeeeeeeeee.

M eeee ee eee Meeeeee eeeeeee eee eeeeeeee eeee MeM8 (8.88 e, 88.8 eeee) eee eeeeeeee (8.88 eM, 88.8 eeee) ee MM8Me8 (88 eM). Mee eeeeeeeee eeeeee eee eeeeeee ee ee eeeee M8 eee 88 eee eeeeee eeeeee e eeee ee eee β-eeeeeee eeeeee ‌888‌ (M8 = Me; M8 = Me; M8 = M; M8 = Me; 8.88 eeee) ee MM8Me8 (8 eM). Mee eeeeeeee eee eeeeeeeee eee ee eeeeeeeeee 88 eee ee ee eee eeeee M8. Mee eeeeeee eee eeeeee eeee Me8M (888 eM) eee eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eeee eeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeeeeee eeeeeee Meeeeeee eee eee eeeeeee eee eeeeeee ee eeeee. Mee eeeeeeee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee; eeeee: 8.888 e (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 88.