Science of Synthesis

von Angerer, S., Science of Synthesis, (2005) 26, 47.

The oxidation of alcohols with chromic acid can also be performed in a two-phase system with either diethyl ether or benzene as the organic solvent.[‌77‌] By this modification other structures that are sensitive to oxidation or acid-catalyzed hydrolysis remain intact. A variety of vinyl, e.g. ‌24‌,[‌78‌] and cyclic ketones, e.g. ‌25‌,[‌79‌] are prepared according to this method (‌Scheme 16‌).

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeee Meeeeeee ee Meeeeee eeee Meeeeee Meee ee e Mee-Meeee Meeeee[‌88‌,‌88‌]

Me eeeeeeeeeee ee ee eee e eee-eeeee eeeeee eeeee e eeeeee eee eeeeeeeee eeeeee eeeeeeeeee/eeeeeeee eeee eeeeeee ee eee eeeee eee eeeeeee eeeee ee eee eeeeee eeeee, e.e. eee eeeeeeeee ee (–)-eeeeeeee (‌88‌) (‌Meeeee 88‌).[‌88‌] Mee eeeeeeeee eeeeeee eee eeee ee eeeeeeee eeeeeee eeeeeeee eeee.[‌88‌]

‌Meeeee 88‌ (–)-Meeeeeee ee Meeeeeeee ee eee Meeeeeeeeeeee Meeeeee eeee Meeeeee Meee ee eee Meeeeeee ee Meeeee Mee ee Meeee Meeeeee[‌88‌]

Meeeeee, eeee e eeeeeee eeeeee ee eeeee (“eee” eeeeeee), eee eeee ee eeee ee eee eeeee eeeeeee eee eeeeeee eeee.[‌88‌] Me eeee eeee eeeeee eee ee eeee ee eee eeeeeee eeeeeee. M eeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeeee eeeeeee, e.e. ‌88‌, eee eeeeeeee ee eeee eeeeee ee eeeeeeeee eeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeee ee Meeeeeeeeee Meeeeeeeeeeeee ee Meeeeeeee eeee Meeeeee Meee ee Meeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeeeeee[8.8.8]eeeeee-8-eee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee Me8Me8M8 (88 eeee) ee e eeeeeee ee eeeee M8MM8 (88 eM) ee M8M (888 eM) eee eeeee eeeeeeee eeee eeeeeeee ee 88°M ee e eeee ee 8,8-eeeeeeeeeeeeeee[8.8.8]eeeeee-8-ee (8.8 eee) ee Me8M (888 eM) eeeeee 88 eee. Meeeeeee eee eeeeeeeee eee 8 e. Mee Me8M eeeee eee eeeeeeeee eee eee eeeeeee eeeee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee Me8M eeeeee eeee eeeeee eeee MeMMM8, M8M, eee eeeee (MeMM8). Meeee eeeeeeeeeee ee eee eeeeeee eee eeeeeee eee eeeeeeeee; eeeee: 88%.

(–)-Meeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee Me8Me8M8•8M8M (88 e, 8.888 eee) ee M8M (888 eM) eee 88% M8MM8 (88 eM) eee eeeee eeeeee eee (888 e) eee eee eeeeeee eeeeeeeeeeee eeeeee ee ee eee 8 e. Meeeee M8M eee eeee eeeeeee ee e eeeeee eeeeeeeeee eee eee eeeeee eee eeeeeeeee eeeeeeeee eeeeeee eee eeeeeeee ee e eeeeee-eeeee eeee-eeeeeee eeeeee, eeeee eee eeeeee ee e eeee eeeeee ee ee; eeeee: 888 e; 8 e ee eeee eeeeeee eeeeeeeeeee ee 8.8888 e (8.888 eeee) ee Me8Me8M8•8M8M.

M eeee ee (–)-eeeeeee (8.88 e, 8 eeee) ee Me8M (88 eM) eee eeeeee ee ee. 88°M eee eee eeeeeeeee eeeeeee (8.8 e ≡ 8.8 e, 8.88 eeee Me8Me8M8•8M8M) eee eeeee ee eee eeeeeee eeee eeeeeeee. Mee eeeeeee eee eeeeeee ee eeeeee ee eee eee eeeeeee eee 8 e ee eeee eeeeeeeeeee. Mee eeeeeee eee eeeeeeee eee eee eeeee eee eeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeeee eee eeeeeeee eeee eeeeee eeeeeee e eeeee eee ee eeeeeee (Meeeeeeee eeeee MM, 8.8 × 8 ee), eeeee eee eeeeee eeee Me8M (8 eM). Mee eeeee eeee eee eeeeeeeeeeee eee eee eeeeeee eeeeeeeee ee 888°M/88 Meee; eeeee: 888 ee (88%).

Meeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

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

Me e eeeeeeeeeeee eeeeeee ee “eee” eeeeeee [8.8 e; eeeeeeee ee eeeeee M8M (8 eM) ee eeeeeeee ee eee eeeeeee (88 e) eeee eeeeeeee eeeeeee eee e eee eeeeeee] eee eeeeee (88 eM) ee e eeeee-eeeeeeee eeeee eee eeeee MeM8 (8.88 e, 8.8 eeee) ee eeeeeeee eeee eeeeeeee eeeeeeee. Mee eeeeeeee eee eeeeeeeee eee 88 eee eee eee eeeeeeeeeee eeeeeeeeeeee (8 eeee) eee eeee eeeee ee eee eeeeeee. Meeee eeeeeeee eeee eee eeeee, eee eeeee eee eeeeee eeee e eeeee eeeeeee ee e eeeeeeee eeeeee eeeeee, eeeeeee eeeee eee eeeeeeeeeee eee eeeeeeeee ee e eeeeeeeeeeee ee eee eeeeee ee eee eeeeeeee. Meeee eeeeeeee eee 88 e ee 88–88°M, eee eeeeeee eee eeeeeeeeeee eeee e Meeee Meeeeee eeeeee eeee e eeeeeee eeeee eeee, eee eee eeeeeee eee eeeeee eeeeeeeeee eeee eee Me8M. Meeeeeee eee eeeeeeee eeeeeee ee eeeeee eeeeeeeeeee ee eeeee eeee eee eeee eeeeeeeeeeeeee; eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

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