Science of Synthesis

Mourad, A. K.; Czekelius, C., Science of Synthesis Knowledge Updates, (2011) 3, 70.

1,1,1-Trihalides are typically hydrolyzed under acidic conditions;[‌71‌,‌72‌] however, N′-hydroxyimidamides (amidoximes)[‌73‌] and strongly basic or hydrothermal conditions[‌74‌] have also been employed. Aliphatic as well as aromatic compounds are suitable substrates for this method. However, while the hydrolysis of 1,1,1-trichlorides, such as the conversion of 2,6-dichloro-3-(2,2,2-trichloroethyl)pyridine (‌35‌) into 2-(2,6-dichloropyridin-3-yl)acetic acid (‌36‌), is quite common (‌Table 8‌), the related transformations involving compounds incorporating fluorine or the heavier halogens are limited in number. The protocols can be extended toward the formation of the corresponding carboxylic esters in the presence of alcohols.[‌75‌] Furthermore, aromatic 1,1,1-trichloromethane derivatives can be converted into the acid chlorides using sulfur dioxide.[‌76‌]

‌Meeee 8‌ Meeeeeeeee ee 8,8,8-Meeeeeeeeeeeeeee Meeeeeeeeee[‌88‌,‌88‌,‌88‌–‌88‌]

Meeeeee Meeeeeee	Meeeeeeeee	Meeeeee	Meeee (%)	Mee
	MMM8 (eeeeee), M8M8, 88–88°M		88	[‌88‌]
	MM, M8M		88	[‌88‌]
	88% M8MM8, 888°M, 8 e		88	[‌88‌]
	8-M8MM8M8M(MM8)MMM, eeeeeeee, 888°M		88	[‌88‌]
	M8MM8 (8% MM8), ee, 88 e		88	[‌88‌]
	88% eeeee, ee, 8 e		88	[‌88‌]
MeMMe8	M888M, eeeeee	MeM88M8M	88	[‌88‌]

Mee eeeeeeeeeeeeeee eeeee ee eeeee eeeeee eeeeee eeeeee eeeeeeeeee eeeeeeeeee. Meeeeeeee, eeeeeeeeee ee eeeee eeeeeeeeee eeee eeeeeeeeeee ee eeeeeeee ee eee eeeeeeee. Me eeeeeeee, eeeeeeee 8,8,8-eeeeeeeeeeeeeeee eeeeeeeeeee eee ee eeeeeeeeee ee eeee eeeeeeeeee eeeee eeeee eeee eeeeee eeeee ee eeeee. Mee eeeeeee, 8-eeeeee-8-(eeeeeeeeeeeeeee)eeeeeeeee (‌88‌) eee ee eeeeeeeee eeee 8-eeeeeeeeeeeeeee-8-eeeeeeeeee eeee (‌88‌) eeeee 88% eeeeeeee eeee ee eeee eeeeeeeeeee (‌Meeee 8‌).[‌88‌–‌88‌]

‌Meeee 8‌ Meeeeeeeee ee 8,8,8-Meeeeeeeeeeeeeee Meeeeeeeeee[‌88‌–‌88‌]

Meeeeeee Meeeeeee	Meeeeeeeee	Meeeeee	Meeee (%)	Mee
	88% M8MM8, eeeeee		88	[‌88‌]
	M8M8, 88% eeeee		88	[‌88‌]
	88% M8MM8, 888°M		88	[‌88‌]
	eeeee, 888°M		88	[‌88‌]
	88 M MeMM, 88–88°M		88	[‌88‌]

Meeeeeeee eee eee eeeeeeeeee ee 8,8,8-eeeeeeeeeeeeeee eeeeeeeeeee eeee eeee eeeeeeee eeee eeeeee eeeeeeee eeeeee, eeeeeeeee eeeeeeeeee, eee eeeeeee, eeeeee eeeeee eeee[‌88‌] ee eeeeee(M) eeeeeee[‌88‌,‌88‌] eee eeeeee eeee. Meeee eeeeee eeeeeeeeee eeee eeee eeee ee eeeeeee eeeeeeeeee ‌88‌ eeee eeeeeeeeee eeee ‌88‌ (‌Meeeee 8‌).

‌Meeeee 8‌ Meeeeeeeee ee 8,8,8-Meeeeeeeeeeeeee Meeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

8-(8,8-Meeeeeeeeeeeeee-8-ee)eeeeee Meee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeeeeee ee 8,8-eeeeeeeeeeeeeeee ‌88‌ (88 e, 8.888 eee) ee 88% M8MM8 (88 eM) eee eeeeee ee 888°M eeee eeeeeeee eeee eee eeeeee ee 8 e. Mee eeee eeeeee eee eeee eeeeee eeee e eeeeeee ee 888 e eee/M8M. Meeeeeeeee eeee eee eeeee eeeeeee (eeeee: 8 e) eee eee eeeeeeee eee eeeeeeeee eeee MeMMe (8 × 888 eM) ee eeee eeeeeee eeeee eeeeeeee (eeeee: 8.8 e). Meeeeeeeeeeeeeeee ee eeee eeeee eeeeeeee [eeeeeee (MMMMMMM: eeeeeeeeee); 888 eM] eeee eee eeeeeee; eeeee: 8 e (88%).

8-Meeeeeeeeeeeeee-8-eeeeeeeeee Meee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8-(eeeeeeeeeeeeeee)eeeeeeeee ‌88‌ (88.8 e, 88.8 eeee) eee 88% M8MM8 eee eeeeee ee 888°M eee 88 eee. Me eee eeee eeeeeee ee eeee eee 8 M MeMM eee eeeee eeeee eM 88 eee eeeeeee. Mee eeeee eeeeeeee eee eeeeeee ee eeeeeeeeee eee eeeeee eeee e eeeee eeeeee ee M8M eee MeMM. Mee eeeeeeee eee eeeeeeeee eeee eeeee MMe eeeee eM 8 eee eeeeeee, eee eeee eeeeeee ee eeeee eee eee eeeee ee ee. Mee eeeeeeeee eeeeeee eee eeeeeeee, eee eee eeeee eeeeeeee eee eeeeee eeee M8M eee eeeee eeeee eeeeee ee eeee eee eeeeeee; eeeee: 8.8 e (88%).

Meeeeee[(8-eeeeeeeeeeeee)eeeeeeeeeeeee]eeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Meeeeeeeee ‌88‌ (8.8 e, 8.88 eeee) eee eeeeeeeee ee e eeeeeee ee eeeeeee (88 eM), MMM8M (8 eM, 88 eeee), eee M8M (8 eM). MeMM8 (8.8 e, 88.8 eeee) eee eeee eeeee eee MeMe eeeeeeeeeee eeeeeeeeeeee eeee eee eeee. Me eeeee ee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeeee eeeeeeeee. M eee. eeee ee MeMe eee eeee eeeee ee eeeeeee eee eeeeee MeMM8, eee eee eeeeeee eee eeeeeeee. Mee eeeeeeee eee eeeeeeeee eee eee eeeeeee eee eeeeeee ee eeee eee eeeee eeeeeee. Meee eeeee eeeeeeee eee eeeeeeee ee eeeeeeeeeee ee MMM eee eeee eeeeeeeee eeee M8M. Mee eeeeeeeeeee eeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeee eeeee eeeeee ee eeee eee eeeeeee; eeeee: 8.88 e (88%).

References