Science of Synthesis

von Angerer, S., Science of Synthesis, (2005) 26, 44.

Addition of acetic acid to chromic acid or chromic/sulfuric acid mixtures often has a favorable effect on oxidation reactions due to an increased solubility of the reactants. Alternatively, chromium(VI) oxide is dissolved in acetic acid to afford a mixed anhydride as the oxidizing reagent. One of the early examples of this procedure is the preparation of ­tropinone (‌15‌) from tropine (‌14‌) (‌Scheme 10‌).[‌57‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeee ee Meeeeeeee eeee Meeeeeee(MM) Meeee ee Meeeee Meee[‌88‌]

Meee eeeeeeee eee ee eeee eee eee eeeeeeeeeee ee eeeeeee eeee eeeeeee eeeeeeeee eeeeeeeeeeeeeee, eeee ee eeeeee eeeee[‌88‌,‌88‌] ee eeeeeee eeeee,[‌88‌] ee eee eeeeeeee. Meeeeee ‌88‌[‌88‌] eee ‌88‌[‌88‌] eee eeeeeeeee eeee ee eeeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeee ee eee Meeeeeeee ee Meeeeeee eeee Meeeeeeee Meeeeeeeeeeee ee eee Meeeeeee[‌88‌,‌88‌]

Meeeeeee(MM) eeeee ee eeeeee eeee ee eeee eeeeee eee eee eeeeeeeee ee α-eeeeeee eeeeeee eee eeeeee ee eeeeeeeee[‌88‌] eee α-eeeeeeeeeeeeeee,[‌88‌] eeeeeeeeeeee. Meeeeeee eee eeeeeeeeeee-8,8-eeeee[‌88‌] eee M-eeee-eeeee-8-eeeeeeeeeeeeeee.[‌88‌] Me e eeeeeee eee 8-eeeeeeeeeeeeeeee-8-eeeeeeeeee-8(8M)-eee (‌88‌) ee eeeeeeee ee eee eeeeeeeeeeeee eeeeee ‌88‌ eeeeeee eeeeeeee ee eee eeeeeee eeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee Meeeeeeee ee e Meeeeeeee Meeeeee Meeee ee eee Meeeeeee ee e Meeeeee Meee[‌88‌]

Meee eeeeee eeee ee eeee ee eee eeeeeee eee eee eeeeeeeee eeee eeeeeeeee eeeeeeeeee eeeeeeeee eee eeeeeee. M eeeeee ee eeeeeeeeeeeeeee eeeeeee, e.e. ‌88‌, eeee eeeeeeeee eee eeeeeeee eeeeeeeeeeee eee eeeeeeeeeee eeee eeeeee eeeeeeeeee ee eeeeee eeee ee eeee eeeee eeee eeeeeeeee ee eee eeeeeeeeeeeeeee eeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeee ee Meeeeeeeeeeeeee Meeeeee ee Meeeeeeee eeee Meeeee Meeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeee (‌88‌):[‌88‌]

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

Me ee e eeee ee MeM8 (88 e, 8.88 eee) ee M8M eee eeeeeee MeMM (88 eM) eee eeeee eeeeeeee eeee 8 e ee e eeee ee eeeeeee (‌88‌; 88 e, 8.888 eee) ee eeeeeee MeMM (888 eM). Meeee eeeeeeee eee eeeeeee eee eeeeee ee e eeeee eeee eee e eeeee eeeeee ee eeee. Meeee eeeeeee, eee eeeeeee eee eeee eeeeeeee eeee MeMM eee eeeeeeeee eeeeeee eeeee eeee Me8M. Mee Me8M eeeee eee eeeeee eee eeeee. Meeee eeeeeeeeeee ee eee eeeeeee eee eeeeeee eee eeeeeeeee ee eeee eee eeeee eeeeeeee; eeeee: 88.8 e (88%); ee 888–888°M/888 Meee; ee 88–88°M.

Meeeeeeeeeeeeee Meeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M eeee eeeeeeee ee eeeeeeeeee Me8Me8M8•8M8M (888 ee, 8 eeee) eee M8MM8 (888 ee, 8 eeee) ee eeeeeee MeMM (8 eM) eee eeeee eeeeeeee ee e eeeeeee eeee ee eee 8,8,8-eeeeeeeee­eeeee-8-ee (8 eeee) ee MeMM (8 eM). Meeee 88 eee ee ee, eee eeeeee eeeeeee eee eeeeeeee ee eeeeeeee ee eMeMM (8.8 eM), eee eee eeeeeee eee eeeeeee eee ee eeeeeeeeee 88 eee. Mee eeeeeee eee eeeeee eeee eeeee (88 eM) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Meeee eeeeeee eeee ee MeMMM8 (8 × 88 eM) eee eeeee (88 eM), eee eeeeeeee eeeeeee eeeeeeee eeee eeeee (Me8MM8) eee eee eeeeeee eeeeeee ee eeeeeeeeeeee ee eeeeeeeeeee eeeeeeee ee eeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee ee eeeeee eee eeeeeee ee eeeeeeeee eeee; eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

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