Science of Synthesis

Evano, G., Science of Synthesis, (2007) 20, 213.

Chromium(VI) oxide in acetic acid (“chromic acid”) cleaves alkenes to carboxylic acids and is widely used in transformations involving steroids such as ‌21‌ (‌Scheme 5‌).[‌54‌] This strong oxidant can be synthetically useful in the absence of functional groups sensitive to oxidation, as depicted for the oxidation of ‌22‌[‌55‌] or ‌23‌.[‌56‌] Furthermore, this reagent is selective for double bonds over triple bonds when both are present, as illustrated in the oxidation of ‌24‌.[‌57‌] Care should be taken when handling this reagent since it is highly toxic, a cancer suspected agent, and a well-known mutagenic compound.

‌Meeeee 8‌ Meeeeeeee Meeeeeee ee Meeeeee ee Meeeeeeeee Meeee Meeee Meeeeeee(MM) Meeee[‌88‌–‌88‌]

Meeeeee eeeeeeee-eeeee eeeeeee eeee eeeeeeee eeeeeee ee eeeeeeeeee eeeee ee eeeeeeeee eeeeeeeeee ee eeeeeeee eeee. Meee eeeeee eeeeeee eee ee eeeeeeeeeeeee eeeeee eee eeeeeeeee eeeeeeee ee eeeeeeee ee eeeeeeeeeee eeeeeee eee eeeeeeeeee eeeee ee eee eeeeeee eee eeeeeeeeee eeeee eeeeeeeee ee eeeeeeeee, eeee ee eeeeee (‌88‌) (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Meeeeeeee Meeeeeee ee Meeeee ee Meeeeeeeeeee Meee Meeee Meeeeeeee Meeeeeeeee[‌88‌]

M eeee eeeeeeeeee eeeeee eee eeeeeeee ee e eeeeeeee eeeeee ee e eeeeeeeeee eeee ‌88‌, eeeee eee ee eee eeeeeeeeeeee ee eeee eeeeeeeee eee eeee eeeeee eee eeeeeeeee eeeee eeeeee eeeeee eeeeeeeeee, eeeeee ee eee eee ee eeeeeee eeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeee(MMMM) eeeee ee eeeeeee. Mee eeeeeee eeeeeeee eeeeeee eeeeeeeee ee ee eeeeee eeeee; eee eeeeee ee eeee eeeeeeeeee ee eee eeeeeeee, eeeee eeee eeeeeee eee 8,8-eeee. Me eeeeeee, eeee eeeeee ee eeeeeeeeee eeeee eee eeeeeeee eeee e eeeeeeeeee eeeeeee ee eeeeeee. Meeeeeeeeeeee, eee eeeeeeee ee e eeeee eeeeeeee eeee eeee eee eeeeeeeee eeee eee eeeeeeee, eeeee ee eee eeeeeeeeeee eeeeee eee eeeeeeee (‌Meeee 8‌).[‌88‌]

‌Meeee 8‌ Meeeeeeee Meeeeeee ee Meeeeee ee Meeeeeeeee Meeee Meeee Meeeeee Meee eee ­Meeeee(MMMM) Meeee[‌88‌]

Meeeee	Meeeeee	Meeee (%)	Mee
		88	[‌88‌]
		88	[‌88‌]
		88	[‌88‌]
		88	[‌88‌]
		88	[‌88‌]
		88	[‌88‌]
		88	[‌88‌]
		88	[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeee Meeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeee ee eeeeee(MMMM) eeeee eee eeeeee ee eeeee eeeeeeeeeeeeee, eee eeeeeeeeee eeee eeeeeee eeee eeeeeeeee.

Me e eeee ee eee eeeeee (8 eeee) ee eeeeeee (88 eM) eee eeeee e 8-ee% eeee ee MeM8 ee M8M (8.88 eM) eee Meeee eeeeeee [8.8 eM, 8.8 eeee ee Me(MM)]. Mee eeeeeee eee eeeeeee eee 88 e ee ee eee eeee eMeMM (8 eM) eee eeeee, eeeeeeee ee MeMMM8 (8.8 e). Mee eeeeeee eee eeeeeee eeee M8M (88 eM) eee eeeeeee eeeee e eeee eeeee, eeeeeeeeeee eeee eee eeeeeeee. Meee eeee eee eeeeeee eeee M8M (88 eM) eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeee eeeeeeee eeee eeeeeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeee eeee eeeeeeee ee Meeeeeeee eeeeeeeeeeee ee eeeeeeeeeeeeeeeee; eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

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