Science of Synthesis

von Angerer, S., Science of Synthesis, (2005) 26, 46.

An alternative solvent, which is widely used for oxidations with chromic acid, is acetone. This oxidizing system has been termed the Jones reagent[‌65‌] and its use as an oxidizing agent is a standard procedure in organic syntheses. Generally a solution of chromic acid in dilute sulfuric acid is added to a solution of the secondary alcohol in acetone. The dilution of the chromic acid in the course of the reaction minimizes overoxidation. Excess oxidizing agent can be destroyed with propan-2-ol.[‌66‌] By this method it is possible to oxidize secondary hydroxy groups next to triple bonds, e.g. the formation of oct-3-yn-2-one (‌21‌) (‌Scheme 14‌).[‌67‌,‌68‌] Examples of ketones formed using this reagent are pent-3-yn-2-one (70%),[‌69‌] hex-1-yn-3-one (72%),[‌65‌] and 1-chloropent-1-yn-3-one (83%).[‌69‌,‌70‌]

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Meeee eeeeeeee eeee e eeeeee eeee ee eee 8,8-eeeeeeee eee ee eeeeeeee eeee eee Meeee eeeeeee eeeeeee eee eeeeeeeee ee α,β-eeeeeeeeeee eeeeeee,[‌88‌] eeee eeeeeee eee eeee eeee eeee eee eee eeeeeeeeeee ee e eeeeeee ee eeeeeeeeeee eeeeeeeee eeeeeee.[‌8‌,‌88‌–‌88‌] Me eeeeeee ee eee eeeeeeeee ee eee eeeeeee eeeee ee 8β-eeeeeeeeeeee-8-ee-88-eee (‌88‌) ee eee eeeee ‌88‌ (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeee ee Meeee-8-eee-8,88-eeeee ee Meeeeeeee eeee eee Meeee Meeeeee[‌88‌]

Meeee eeeeeee eee eeeeeeeee eeeeeee eeeeee eeeeeeeee ee eeeeeeeeeeeee eeeeee eeeeeeeee eeeeee eeeeeeeee, eeeeeeeee eeeeeeee eee ee eeeeeeeeeee eeeeeeee ee Meeee eeeeeee ee eee eeeeeeee ee eeeeee eeeeee. Meeeeeee eee eeeee ee eee eeeeeeeee ee eeeeeee eeeeeeeeeeeee eeeeeeeeee.[‌88‌,‌88‌] Meeeeeeee eeeeeeeee eeeeeeeee ee eee ee eee eeeeeeeee eeeeeee eeeeee ee eee eeeeeeee eee ee eeeeeeee eee ee eeeeee eeeeeeeee eeeeee eee ee eee eeeeee eeeeeeeee ee ee eeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

Mee-8-ee-8-eee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

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

M eeee ee MeM8 (88.8 e, 8.888 eee), M8M (88 eM), eee eeeee M8MM8 (8.8 eM) eee eeeee eeee eeeeeeee ee 8–88°M eeeeee 8 e ee e eeee ee eee-8-ee-8-ee (88 e, 8.88 eee) ee eeeeeee (88 eM). Meeee eeeeeeee eeee M8M eee eeeeeee eee eeeeeeeee eeee Me8M eee eeeeeeeee ee eeeee; eeeee: 88.8 e (88%); ee 88.8–88.8°M/88 Meee.

Meeee-8-eee-8,88-eeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

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

M eeee ee MeM8 (88 eeee) ee 8 M M8MM8 (88 eM) eee eeeee ee 88°M eeee eeeeeeee ee e eeee ee 8β-eeeeeeeeeeee-8-ee-88-eee (‌88‌; 8.8 eee) ee eeeeeee (8.8 M). Meeeeeee eee eeeeeeeee eee 8 eee. Mee eeeeee eeeeeeeee eeeee eee eeeeeeeee ee eeeeeeee ee MeMM. Mee eeeeeee eee eeeeee eeee eee-eeee MeMe eeee. Mee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee, eeeee, eee eeeeeeeeeeeeee; eeeee: 88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 88.