Science of Synthesis

Sandford, G., Science of Synthesis, (2007) 31, 37.

Trifluoromethyl hypofluorite (F3COF, ‌15‌)[‌69‌] is a colorless gas that can be prepared from carbonyl difluoride (difluorophosgene), fluorine, and cesium fluoride. Reactions involving trifluoromethyl hypofluorite are carried out at low temperatures, usually −25°C, in an inert solvent, such as trichlorofluoromethane or chloroform, using vacuum-line techniques. A cosolvent (methanol, acetone, etc.) is sometimes added to aid solubility of the substrate, but competing reactions between the cosolvents with the fluorinating agent can cause problems. Radical inhibitors, such as nitrobenzene or 1,2-dinitrobenzene, enhance the selectivity of the reactions.

Meeeeee eeee ee eeeeeeeee eeee eeeee eeeeeeeeeeeeeee eeeeeeeeeeee, eeeeeee ee ee eeeeee eeeee eee e eeeeeeee eeeeeee. Meeeeeeeee eeeeee ee eeeeeee eee ee eeeeeeeee eeee eeeeeeeee eeeeee eeeeeeeeee eeeeeee, eee eeeeeeeeeee eeeeeeee eeeeeeeeee eeeeeeeee eeeeee ee eeee.

Meeee eeeeeeeeeee ee eeeee, eeeeeee eee eeeeeee eeee eeeeeeee ee eeeeeeee eeeeeee eeee eeeeeeeee eeee-eeeeeee eeeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌] Meeeee eeeee eee eeeeeeeee eeeeeeee ee eeeee eeeeeeee eeeeee ee eeeeeeeeeee eeeeeeee eee ee eeeeeeee (e.e., eee eeeeeeeee ee ‌88‌).[‌88‌] Meeeeeeee eeee eeeeeeeeeeee eeeeeee eeeeeee eeeeeeee-eeeeeeee eeeeee eeee eeeeeeee ee eeeeeeee, eee eeeeee ee eeeee eeeeee ee eee eeeeeeeee.[‌88‌,‌88‌]

Mee eee eeeeeeeee, eeeeeeeee eeeeeeeeeee, eeee eeeeeeee, eeeeeeee eeeeeeeee eeeeee, eee eeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeeeeee eeee eeeeeeeee eee eeeeeeeeeee ee e eeeeee, eeeeee eeeeeee eeeeeeeee eeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeee ee Meeeeeeeeeeeeee Meeeeeeeeeee[‌88‌–‌88‌]

Mee eeeeeee eeeeeee eeeeeeeeeeeeeeeee eeeeeeeeeeeeee [M8M(MM)8], eeeeeeeeeee ee eee eeeeeeee ee eeeeee eeeeeee eee eeeeeeee, eee ee eeee ee eeeeeeeeee eeeeeee eeeeeee eeeeeeeeeee (e.e., ‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeee ee Meeeeeeeeeeeeeeee Meeeeeeeeeeeee[‌88‌]

Meeeeee eeeeeee eeeeee, eeeeee eeeeeeeeeeee (MeMM, ‌88‌), eee ee eeeeeeeeeee ee eeeeeeeee ee eeeeee eeeeeee eeee eeeeeeee ee eeeeeeeeeeeeeeeeeeeeee ee −88°M, ee ee eeeeeee eeeeeeee eeee e eeeee eeeeeee ee eeeeeeeee eeeeeee eee eeeeee eeee.[‌88‌,‌88‌] Meeeee eeeeeeeeeeee ee eeeeeee eeeeeeeeeee ee eeeeeeee eeeeeeeeeee eeeeee eee, eee ee eee eeeeeeee eeeeeeee.

Me ee eeeeeeee ee eeeeeeeeee ee eeeeeeeeee eeeeeeee-eeee eeeeeeee eeeeeee eeee ee eeeeeeee ee eeeeeeee eeee eeeeee eeeeeeeeeeee (‌88‌); eeeee eeeeeeeee eee eeeeeee ee ee eeeeeeee–eeeeeeeeeee ee eee eeee-eeeeeeee-eeee eeee—eeeee π-eeee.[‌88‌,‌88‌] Meee eeeeeeeee ee eeeeeeeee ee eee eeeeeeeee ee eee eeeeeeee eeeeeee ‌88‌ eeee 8,8-eeeeeeeeeeee-8-eeeeeeeeeeee (eeeeeeeee, ‌88‌) (‌Meeeee 88‌), eee eee eeee eeeeeeeeee ee 8-eeeeee-8-eeeeeeeeeeeeee eeee ee eeeeeeee eeee eeeeeee (‌Meeee 8‌, eeeee 8).

‌Meeeee 88‌ Meeeeeee Meeeeeee ee Meeeee Meeeeeeeeeee eeee 8,8-Meeeeeeeeeee-8-eeeeeeeeeeee[‌88‌]

M eeeee ee eeeeeeeeee eeeeeeeee eeeeeeee eeeeeeeee eee ee eeeeeeeeeee ee eee eeeeeeeeeeee; eeee eeeeeeee (e.e., eee eeeeeeeee ee ‌88‌) eee eeeeeeeee ee ‌Meeee 8‌.

‌Meeee 8‌ Meeeeeeeeeeee ee Meeeeeeee Meeeeeee Meeeeeeee ee Meeeee Meeeeeeeeeee[‌88‌–‌88‌]

Meeee	Meeeeeeee	Meeeeee	Meeee (%)	Mee
8	MeMMe		88 (e/e 8:8)	[‌88‌,‌88‌]
8			88	[‌88‌,‌88‌]
8			88	[‌88‌]
8			88 (8.8:8)	[‌88‌]
8			88	[‌88‌]
8			88	[‌88‌]
8			88	[‌88‌]

Meeeeeee eeeeee eeeeeeeeeeee ee eeeeeeeeeee ee eeeeeeeee eeeeeee eee eee eeeeeeeeeeee ee eeeeeeeee eeeeeeee eeeeeee, eee eee ee eeeeeeeeeeeeeeeeee (MMM) eeeeeeee ee eeeeeeee eeeee eeeeee eee eeeeeeeeeeeee eeeeeee ee eeeeeeeeee eeeeeeeeeeee eeee eeeeeee eee eeeeeeeeee eee ee MMMe.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeee Meeeeeeeeeee (‌88‌):[‌88‌]

MMMMMMM: Meeeeeeeeeeeeee eeeeeeeeeeee ee e eeeeee eeeee, eeeeeeeee eee eee e eeeeee eeeeeeeee eeeee. Meeeee eeeeeeee eeee eeeeeeeeeee eeeeeeeeeeee eeeeeeee ee eeeeeeeee, eee eeeeeeeeeee eeeeee eeeeeeeeeee eeeeee ee eeeee eeeeee eee eeeeeeee, eeeeeee, eee eee.

MMMMMMM: Meee eeeeeeee eee ee e eeee eeeeeeee eeeeeeeee eeeeeee eee eeeeee eeeeeeeee ee eeeeeeeeeee eeee e eeee eeeee ee eeeeeeeee. Me ee e eeeeee eeeeeeee ee eee eeee, eeeeee eeeeeeeee, eeee, eee eeeee.

MMMMMMM: Meeeeeee eeeeeeeeee ee e eeeeeeeee, eeeeeee, eee eeeee eee. Me ee eeeeee eeeeeeeeee ee eee eeeeeee.

M eee, 888-eM Meeee eeeeeeeee eee eeeeeee eeee eee MeM (88 e, 88 eeee) eee 88 88-ee-eeeeeeee eeeeeeeee eeeee eeee eeeeeeee. Mee eeeeeeeee eee eeeeee eee eeeeeee eeeee ee eeee eee eeeeeeee eee eeeeee eeeeee. MMM8 (8.88 eeee) eee eeeeeeeee eeee eee eeeeeeeee eeeeee ee eeeeee-eeeeeeee eeeeeeeeee, eee eeeeeee eeeee eee eeeeee ee 88 M, eee M8 (8.88 eeee) eee eeeeeeeeee. Mee eeeeeee eee eeeeee ee 888 M, eeeeeee ee eeeee eee 8 e, eeee eeeeee eeeee ee 88 M. Meeeee M8 eee eeeeeeee eeeeeee e eeee eeeeee eeee eeee eeee. Mee eeeeeeeee eee eee eeeeeeeeeee ee e eeeeeeee ee eeeeee eeee ee eeee ee eeeeeeeeeee eeee eeeeeeeee eee; eeeee: 8.88 e (eeeee).

M-[8-Meeeee-8-(eeeeeeeeeeeeeee)eeeeee]eeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeeeeeeeee eeeeeeeeeeee ee e eeeeee eeeee, eeeeeeeee eee eee e eeeeee eeeeeeeee eeeee. Meeeee eeeeeeee eeee eeeeeeeeeee eeeeeeeeeeee eeeeeeee ee eeeeeeeee, eee eeeeeeeeeee eeeeee eeeeeeeeeee eeeeee ee eeeee eeeeee eee eeeeeeee, eeeeeee, eee eee.

M8MMM (88.8 e, 8.888 eee) eee eeeee eeee 8 e ee e eeee ee 8.88 e·e−8 eee eeee eee 8 e ee 8.88 e·e−8 ee e eeee ee M-[8-(eeeeeeeeeeeeeee)eeeeee]eeeeeeeee (88 e, 88 eeee) ee MeMM (88 eM). Mee eeeeeee eee eeeeeeee eeeeeee e eee ee MM eeee, eee eeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee ee MMMe8. Mee MMMe8 eeee eee eeeeee eeee M8M (8 × 88 eM), eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8); eeeee: 8.8 e (88%); ee 888–888°M.

Meeeee Meeeeeeeeeee (‌88‌):[‌88‌,‌88‌]

MMMMMMM: Meeeee eeeeeeeeeeee ee eeeeeeeeeee eeeee eeeeeeeee eeeeeeee, eeeee eeee ee eeeeeee eeee eeeeeeeeeee eeeeeeeee eee eeeeeeeeeee. MeMM eee e eeeeeee eeeeeeee ee eeeeeeee, eee ee e eeeeee eeeeeeeee eeeee eeee ee eeeeeeeeeee eeeeeeeee. Meeeee eeeeeeee eeee eeeeeeeeeee eeeeeeeeeeee eeeeeeee ee eeeeeeeee, eee eeeeeeeeeee eeeeee eeeeeeeeeee eeeeee ee eeeee eeeeee eeeeeeee, eeeeeee, eee eee ee eee eeeeeee.

M 88 eee% eeeeeee ee M8 ee M8 eee eeeeee eeeeee eeeeeee e eeee-eeeeeee eeeeeeeeee ee MeMMe eee MeMM (8:8 eeeee eeeee, 88 e) ee MMMe8 (888 eM) ee −88°M. Mee eeeeeeeeeeeee ee eeeeee eeeeeeeeeeee eee eeeeeeeeee ee eeeeeeee eeeeeeee ee eee eeeeeee eeee eeeeee MM eeee eee eeeeeeeee eee eeeeeeeee M8 eeee ee Me8M8M8.

8-Meeeee-8-eeeeeeeeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

M eeee eeee (−88°M) ee 8-eeeeeeeeeeeeeeeeee (8.88 e, 88 eeee) eee eeeee ee e eeee ee MeMM (8.88 e, 88 eeee) ee MMMe8. Mee eeeeeee eee eeeeeee ee −88°M eee 8 e eee eeee eeeeee eeee M8M (888 eM). Mee eeeeeee eeeee eee eeeeee eeee eee ee MeMMM8 eee M8M eeeee eeeeeee, eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee 8:88); eeeee: 8.88 e (88%).

References

Meeeeee Meeeeeeeeee

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