Science of Synthesis

Wicha, J., Science of Synthesis, (2009) 48, 195.

S-Methyl xanthates are the most common derivatives of secondary alcohols for radical deoxygenation process. These derivatives are prepared by sequential activation of the alcohol with a strong base, reaction of the resulting alkoxide derivative with carbon disulfide, and quenching of the intermediate dithiocarbonate anion with iodomethane. Methyl 1H-imidazole-1-carbodithioate can also be used to prepare S-methyl xanthates.[‌176‌] The intermediate xanthates can normally be isolated and purified.

Meeeeeeee eeeee eeeeee eeee eeeeeeeeeee eeeeeee eeee ee eeeeeeeee M-eeeeee- ee M-(eeeeeeeeee) eeeeeeeeeeeeee eeeeeeeeeee;[‌888‌] eeeeeee, eee eeeeeeeee ee eeeeeee eeeeeeee eeeeee ee e eeeeee eeeeeeeeeee eeee eeeeeeee eeeeee eeee eeee eee eeeeeeeeeeeee eeeeeeee-8-eeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeee eeeeeeeeeee.[‌888‌]

Meeeee eeeeee eeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee ee eeeeeeeee ee eeeeeeeeeeeeeee ee eeee ee eeeeee eeeeeeeeeee ee eee eeeeeeeee eeee eeeeeeeeeee eeee ee eeeeeeeeee eeeeeeeeee eeeeee eee eee eeeeeeeee ee M-eeeeee eeeeeeeee.[‌888‌,‌888‌] Meee eeeeeeee ee eeeeeeeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeeeee α-e-eeeeeeeeeeeee eeeeeeeeee ‌88‌ eee ee M-eeeeee eeeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌] Me eeee eeeeeeeeee, eee eeeeeee ee eeeeeeeee eeee eee eeee ee eee eeeeeeee ee eeeeee eeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee ee α-e-eeee-Meeeeeeeeeee Meeeeeeeee[‌888‌]

M eeee eeeeeeeeee eeeeeeee eee-eeeee eeeeeeeee eeeeeeeeeeeee eeee ‌88‌ (‌Meeeee 88‌) ee eeeeeeeeeee eeee eee eeeeeeeeeeeee M-eeeeee eeeeeeee ee eeeeeeeee eeee eeeeeeeee eeeeeee eee eeee eeeeee eeeeeeeee eee eeeeeeeeeee. Meeeeeeee ee eee eeeeeeee eeee eeeeeeeeeee eeeeeee ee eee eeeeeeee ee 8,8′-eeeeeeeeeeeeeeeeeeeeee eee eeeeeeeeee eeeeeeeee ee eee eeeeeee eeee eeeeeeeeeeeeeeeeee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeeee ‌88‌ ee 88% eeeeeee eeeee. Meee eeee eee eeeeee eeeeeeeeeeeee ee ‌88‌ eeeee eee ee eeeeeeeeeeee eeeee Meeee–Meeeeee eeeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee e Meeeeeeeee Meeeeeee Meeeeee eee Mee M-Meeeee Meeeeeee Meeeeeeeee[‌888‌]

M eeeeee eeeeeeeeee eeeeeeee eeeeeeeee eeeeeee eeeee ee eeeeeeeeee M eeeeeeeeee ‌88‌ (‌Meeeee 88‌) ee eeeeeee eeeeeee eeeeeeeee ee eee M-eeeeee eeeeeeee ee eeeeeeeee eeee eeeeeeeee eeeeeee eee eeee eeeeee eeeeeeeee eee eeeeee eeeeeee, eee eeeeeeeeee eeeeeeeee eeee eeeeeeeeeee eeeeeee ee eeee eeeeeeeeee M eeeeeeeeee ‌88‌.[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee e Meeeeeeeee M Meeeeeeeee eee Mee M-Meeeee Meeeeeee[‌888‌]

Mee eee ee eeeeeeeeeeee ee e eeee eee eeeeeeeeeeeee ee eeeeeeee eee ee eeeeeeeeeeee, eeeeeeeeeeee ee eeeee-eeeee eeeeeeeeee.[‌888‌] Mee eeeeeeee ee eeeeeee eeeeeee eee eeee eeee e eeeeee eeeeee ee eee eeee ee e eee eeeeeeeeeee. Mee eeeeee ee eeeeeeeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeee ‌88‌ eeee eee eeeeeeeeeeeee eeeeeeeee eeeeeee ‌88‌; eee eeeeeee ee ee eeeeeeeeeeee ee eee eeeee eeeeeeeee ee eee-α- eee -β-eeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee ee Meeeeeeeeeee Meeeeee ee eee Meeee Meeeeeeee ee Meeeeeee[‌888‌]

Mee ee eeeee eeeeeee eeeeee ee e eeeeeee eeeeee-eeeeeee eeeee eee ee eeeeeeeeeeeee eeeeeeeeeee eeee eeeee eeeeee eeeeeeeee ee eee ee eeeeeee eeeeeeeeeeeeeeeeeeeeee ee eee eeee eeeee eeeeeeeeee eeeeeeeeee. Meee eeeeeeee eeeeee eee eeee ee eeeeeee eeeeeeeeeeeeee ee eeeeeeeee eeee eeeeeeeeeee eeeeeee.[‌888‌]

8,8-Meeeeeeeeeee[8.8.8]eeeee-8-eee ee eeeeeeeeeeeeeeeee ee eeee eeeeeeeeeee ee eeee ee eee eeee ee eee eeeeeeeee ee eee M-eeeeee eeeeeeee eeeeee eeeeeeeeeeeee ee eee eeeeee eeeeeeeee eeeeeee ‌88‌ ee eeee eeeee eeeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee e Meeeee Meeeeee Meeee 8,8-Meeeeeeeeeee[8.8.8]eeeee-8-eee ee eee Meeeeeeeeeeeee Meee[‌888‌]

Meee eeeeeeee eeeeeeee ee eee eeeeeeeee eee eeeeeeeee ee eeeeeeeee ‌88‌ ee eeeeeeeee eeeeeeee ‌88‌ ee eeee eeeeeeee ‌88‌ eee eeeeeeeee ee ‌Meeeee 88‌.

‌Meeeee 88‌ Meeeeeee Meeeeeee ee Meeeeeeeeeeee ee Meeeeeeee Meeeeeee eee Meeee Meeeeeeeee M-Meeeee Meeeeeeee[‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

M8	Meeeeeeeeeeeee Meeeeeeeee	Meeee (%) ee ‌88‌	Meeeeeeee Meeeeeeeee	Meeee (%) ee ‌88‌	Mee
	8. MeM, MMM, 8°M 8. MM8, MeM, ee	88	Me8MeM (8 eeeee), MMMM (8.8 eeeee), eeeeeee, eeeeee, 8 e	88	[‌888‌]
	8. MeM, MMM, 8°M ee ee 8. MM8, MeM, ee	–	Me8MeM (8.8 eeeee), MMMM (eee.), eeeeeee, eeeeee, 8 e	88e	[‌888‌]
	8. MeMe, MMM, 8°M 8. MM8, MeM	–	Me8MeM (8.8 eeeee), MMMM (8.88 eeeee), eeeeeee, eeeeee, 8 eee	88e	[‌888‌]
	8. MeMMMM, MMM, −88°M 8. MM8, MeM	88	Me8MeM, MMMM (eee.), eeeeeee, eeeeee	88	[‌888‌]

e Meeeeee eeeee eee eee eeeee.

Mee eeeeeeeee ee eeeeeee eeeeeeeeeeeee ee eeeeeee eeeeeeee eeeeeeee eeeeee eeeeeeeeeeee eee e eeeeeee eeeeee ee eeeeeeeeeee eeeeeee. Meeeeeee eeeeeee ee e eeeee eeeee eee M-eeeeee eeeeeeee ‌88‌ ee eeeeeeeee-8-ee eee eeeee ee ‌Meeeee 88‌.[‌888‌] Meee eeee eee eee ee eee 8M-eeeeeeee-8-eeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeee eeeeeeeeeee eeeeeee ee eee M-eeeeee eeeeeeee eeeee e eeeeee eeeee ee eee eeeeeee.

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeee Meeeeeeeeee ee e Meeeeee Meeeeee eeee Meeeeeeeeee Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Mee eeeeee eee ee eeee ee eee eeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeee eeeeeee eeeee ee eeeeee eeeeeeeeeee (‌88‌) (‌Meeeee 88‌).[‌888‌] Meeeeeeee ee e eeeeeeee ee eeee ‌88‌ eeee 8,8-eeeeeeeeeeee[8.8.8]eee-8-eee (8 eeeeeeeeeee) eee eeee ee eeeeee ee eeeeee eeeeeeeee eee eeeeeeeeeee eeeee eee eeee-M-eeeeee eeeeeeee ee 88% eeeee. Meeeeeeee ee eee eeeeeeee eeee eeeeeeeeeee eeeeeee ee e-eeeeee ee 888°M eeeee eee eeeeeeeeeeee eeeeeee ee 88% eeeee. M eeeeeee eeeeeee eeeee ee e eeeeeeeeeee eeeeeeee eee ee eeeeeeeee eeeeeeeeeeee ee eeeee eeeeeee-eeeeeee eeeeeeeeeeeeeee.[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeee Meeeeeeeeeeee ee eee Meeeeee Meeeeee Meeee ee Meeeee Meeeeeeeeee[‌888‌]

Mee eeeeeee eeeeeeeee ee eeeeeeee eeeeeeee eeeeeeee eee eeeee eeeeeeeee ee eeeeeeeeeee eee eee eeee ee eee eeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌] Me e eeeeeee eeeeeeeee, eeeeeee ‌88‌ ee eeeeeeeeeeee eeee eeeeeeeee eeeeeee ee eeeeeeeee eeeeeeeeeeeeeee. (Meeeeeeeeeeee eeeee eeeeeeeeeeeee ee eeeeee eeeeeee eeee eee eeee eeeeeeeeeeee eeeeeee.) Mee eeeeee eeeeeee ee eeee eeeeeee eeee eeeeee eeeeeeeee eee ee eeeeee ee eeeeeeeeeee ee eeee eee M-eeeeee eeeeeeee, eeeee ee eeeeeee eeee eeeeeeeeeee eeeeeee ee eeee eeeeeeeeeee eeeee eeeeeeeeeeeeee–eeeeeeee ee eee eeeeeeeee. Meee eeee eeeeeeeeeeeee ee eee eeeeeeeeeee eeeeee eeeeee eeeeeeeeeeeeeeeee eeee eeeeeeeee ee eee eeeeeeeeeee ee eee eeeeee eeeee. Mee eeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeee ee eee eeeeeeee ee eee eeeeeeee eeeee eeee eee eeee eeeeeeee eeee ee eee eeeeeeee.[‌888‌,‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee e Meeeeeee Meeeeee eee Mee M-Meeeee Meeeeeee Meeeeeeeee[‌888‌]

Meeeeeee eeeeeee eeeeeeeee eee eeee ee eeeeeeee eeeee eeeeeeeee eeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee[‌888‌] ee eeeeeeeeeeeee ee eeeeeeeeeeeeeee.[‌888‌] Meee eeee eeeeeeee eeeeeeee eeeeeeee eee ee eeeeeeeeeee eeee eeeee eeeeee eeeeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeeeeeee eee eeee eeeeeeeeee eeee eee eeee eee eeeeeeeee eeeeeeee.[‌888‌,‌888‌]

Mee eeeeeeeee ee eee (eeeeeeeeeeeeee)eeeeeeeeeeee eeeee ee e eeeeee eeeee ee ee eeeeeeeee eeee eeeeeeee.[‌888‌,‌888‌] Meeee eeeeeee eeeeeeeeee, eeeeeeeeeeee eeeeee eee eeeeeeee eee eeeeeee ee eee eeeeeeeeeeeee eeeeee.[‌888‌,‌888‌] Meeeeee eeeeeeeeeeeee ee e eeeeeee eeeee ee e eeeeeeee α ee e eeeee- ee eeee-eeeeeeee eeee eee eeeee eeee eeeeeee ee eee eeee. Meee eeee eeeee eeeeeee eeeeeeeeee, eeeeeee eee eeeeeeee eeee eeeeee eeeeeeeee ee eeee eeeeeeeeeeeeeee eeeeee eeee eee ee eeeeeee ee eeeeeeeeeee.[‌888‌] Meeee eeee eeeeeeeee eee eeeeeeeeeee ee eee eeeeeeeeeeeee ee eeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meee Meeeeeeee Meee Mee Meeeeeeee eee Meeeeeeee ee Meeeeeeee ee ee M-Meeeee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8-M-Meeeeeeeeee-8-eeeee-8,8-M-eeeeeeeeeee-α-e-eeee-eeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeeeeeee ee eeeeeeeee eeeeeeeee, eee eeeee ee eeeeeeeeee, eeee eeeeeeeeee, eee eeeeeeeee.

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.

MMMMMMM: Meeeeeeeeee eeeeeee ee ee eeeeeeee ee eeee ee eee eeeeeee, eee eeeee ee eeeeeeeee ee eeeeeeeeee; eeeeee eeeeeeeeeeee eee ee eeeee.

MeM (8.8 e, 888 eeee) eee eeeee ee eeeee eeeeeeee ee e eeee ee 8,8-M-eeeeeeeeeee-8,8-M-eeeeeeeeeee-α-e-eeee-eeeeeeeeeeee (88.8 e, 88.8 eeee) ee eeeee MMM (888 eM). Meeeeeeee (888 ee, 8.8 eeee) eee eeeee, eee eee eeeeeee eee eeeeeee ee ee eee 8.8 e. MM8 (88 eM, 888 eeee) eee eeee eeeee eee eeeeeeee ee ee eee eeeeeeeee eee 8.8 e eeeeee MeM (88 eM, 888 eeee) eee eeeee. Meeee e eeeeeee 8.8 e, eee eeeeeee eee eeeeee ee ee eee–eeeee eeee eee MeMM (8 eM) eee eeeee. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeeee ee MeMMe (888 eM). Mee eeee eee eeeeee eeeeeeeeeeee eeee 8 M ee MMe (888 eM), eee. ee MeMMM8 (888 eM), eee eeeee (888 eM), eee eeee eeeee (Me8MM8) eee eeeeeeeeeeee ee eeee eeeeeeee ‌88‌; eeeee: 88.8 e (88%). Meee eeeeeeee eee eeee ee eee eeee eeee eeeeeee eeeeeeeeeeee.

M eeee ee Me8MeM (88 eM, 88.8 eeee) ee eeeeeee (888 eM) eeeeeeeeee MMMM (888 ee) eee eeeee eeeeeeee eeee 8.8 e ee e eeeeeeeee eeee ee eee eeeeeeee ‌88‌ (88.8 e, 88.8 eeee) ee eeeeeee. Meeeeeeee eee eeeeeeeee eee 88 e, eee eeee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88.8 e (88%).

(8′M,8e′M,8′M,8e′M)-8′,8′,8′-Meeeeeeeeeeeeeeeeeeeeee[8,8-eeeeeeeee-8,8′-[8e,8]eeeeeeeeeeeeee] (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeeeeeee ee eeeeeeeee eeeeeeeee, eee eeeee ee eeeeeeeeee, eeee eeeeeeeeee, eee eeeeeeeee.

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.

MMMMMMM: Meeeeeeeeee eeeeeee ee ee eeeeeeee ee eeee ee eee eeeeeee, eee eeeee ee eeeeeeeee ee eeeeeeeeee; eeeeee eeeeeeeeeeee eee ee eeeee.

M 8.8 M eeee ee MeMe ee eeeeeee (8.88 eM, 8.88 eeee) eee eeeee eeee 8 eee ee e eeeeeee eeee ee eeeeeee ‌88‌ (888 ee, 8.888 eeee) ee MMM (8 eM) ee 8°M. Meeee 8 eee, MM8 (8.888 eM, 88 ee, 8.88 eeee) eee eeeee eee eee eeeeeee eee eeeeeee ee eeee ee ee. Meeeeeee eee eeeeeeeee eee 88 eee eee eeee MeM (8.88 e, 8.888 eM, 8.88 eeee) eee eeeee. Meeee e eeeeeee 88 eee, eee eeeeeee eee eeeeeeeeeee eeeeeee Me8M (88 eM) eee M8M (88 eM). Mee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee eee eee eeeeeee eee eeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeeeeeee; eeeee: 888 ee (88%).

M eeee ee eee eeeeeeee (88 ee, 8.888 eeee), MMMM (88 ee, 8.88 eeee), eee Me8MeM (8.88 e, 8.88 eeee) ee eeeeeeeeeeee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeeee eee 88 e. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88 ee (88%).

(8M,8′M,8′M)-8-eeee-Meeee-8′,8′-eeeeeeeee-8,8e,8′,8′-eeeeeeeeee-8M,8M-eeeee[eeeeeeeeeeee[e,e]eeeee-8,8′-eeeee]-8,8(8eM)-eeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeeeeeee ee eeeeeeeee eeeeeeeee, eee eeeee ee eeeeeeeeee, eeee eeeeeeeeee, eee eeeeeeeee.

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.

MMMMMMM: Meeeeeeeeee eeeeeee ee ee eeeeeeee ee eeee ee eee eeeeeee, eee eeeee ee eeeeeeeee ee eeeeeeeeee; eeeeee eeeeeeeeeeee eee ee eeeee.

MMM (8.88 eM, 88.8 eeee) eee MM8 (8.8 eM, 88.8 eeee) eeee eeeee ee e eeeeeee eeee ee eeeeeee ‌88‌ (8.88 e, 8.88 eeee) ee MMM ee ee. Meeee 8 e, MeM (8.8 eM) eee eeeee eee eeeeeeee eee eeeeeeeee eee 8 e. Mee eeeeeee eee eeee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeeee ee MM8Me8. Mee eeee eee eeeeee eeee M8M, eeeee (Me8MM8), eee eeeeeeeeeeee ee eeee eee eeeeeeee, eeeee eee eeee ee eee eeee eeeee eeeeeee eeeeeeeee. M eeeeeee ee eee eeeeeeee, Me8MeM (8.8 eM, 88.8 eeee), MMMM (888 ee), eee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee ee 88°M eee 8 e. Mee eeeeeee eee eeee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8.88 e (88% eeeeeee).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8e, 888.