Science of Synthesis

Wicha, J., Science of Synthesis, (2009) 48, 202.

An alcohol can be conveniently transformed into its 1H-imidazol-1-ylcarbonothioyl derivative under neutral conditions by treatment with 1,1′-thiocarbonyldiimidazole (TCDI), which is available commercially or can be prepared in the laboratory.[‌125‌,‌203‌,‌204‌] 1H-Imidazol-1-ylcarbonothioyl derivatives of secondary alcohols are normally stable and can be isolated and stored; however, those with a hydrogen atom in the β-position undergo fragmentation at higher temperatures to give the corresponding alkenes. Thermal fragmentation of a 1H-imidazole-1-carbothioate followed by catalytic hydrogenation can be used to achieve deoxygenation of complex sterically hindered alcohols.[‌205‌]

Meeeeee eeeeeeeee eeeee eeeeeeeeeee eeeeeeeeee eee eeee eeeeeeeee eeeeeee eeeee eee ee eeeeeeeee eeee eee eeeeeeeeeeeee 8M-eeeeeeee-8-eeeeeeeeeeeeeee eeeeeeeeeee eee eeee eeeeeeeeeeee eeee eeeeeeeeeee eeeeeee ee e eeee eeeeeee eeeee.[‌888‌] Mee eeeeeee, eee eeeeeeeee eeeeeee eeeeeeeeee ‌88‌ eee ee eeeeeeeeeeee eee eee 8-M-(8M-eeeeeeeee-8-eeeeeeeeeeee) ‌88‌ (‌Meeeee 88‌). Meeeeeeee eeeeeeeeeeeee ee eeeeeee eeeeeeee eeeee eee eeeeeeeeeeeee eeeeeeee ee ~88% eeeee, eeeee eeee eeeeeeeee eeeeeeee eeeeeee. M eeeeeee eeeeeeeee ee eee eeeeeeeee, eee eeeeeee eeeeeeeeeee eee eeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeee ee e Meeeeeeee Meeeeee Meeeeeeeee eee Mee 8-M-(8M-Meeeeeeee-8-eeeeeeeeeeee)[‌888‌]

Mee eeeeeee eee eeeeeeeee ee eee 8M-eeeeeeee-8-eeeeeeeeeeeeeee eeeeeeeeeee eeeeeee ee eee eeeeeeee eeeeeeeeee.[‌88‌] Meee eeeeeeee ee e eeeeeeee ee 8M-eeeeeeee-8-eeeeeeeeeeeeeee eeeeeeeeee ‌88‌ eee 8,8′-eeeeeeeeeeeeeeeeeeeeee ee eeeeeee ee e eeeeeeeee eeeeee eeeeeeee ee eeeeeeeeeee eeeeeee ee eeeeeee eeeee eee eeeeeeeeeeee eeeeeee ‌88‌ ee 88% eeeee (‌Meeeee 88‌), eeeeeee eeeeeeee ee e eeeeeeee ee ‌88‌ eee 8,8′-eeeeeeeeeeeeeeeeeeeeee ee eeeeeee ee eeee eeeeeeeeeee eeeeeee ee 888°M eeeeeee ee eeeeeeeee ee eee 8M-eeeeeeee-8-eeeeeeeeeeeeeee eeeeee ee e eeeeee eeeee, eeeeee eee eeeeeee eeeeeeeeee ‌88‌.

‌Meeeee 88‌ Meeeeeeee Meeeeeee eee e 8M-Meeeeeee-8-eeeeeeeeeeeeeee Meeeeeeeee[‌88‌]

Mee eeeeeee eeeee ee eee eeeeeeee β ee eee eeeeeeee eeeee ee eee α-eeeeeeeee-8-ee-eeeeeeeeeee eeeeeeeeee ‌88‌ (e = 8) (‌Meeeee 88‌) eee ee eeeeeeee eeee 8,8′-eeeeeeeeeeeeeeeeeeeeeee eeeee eee eeeeeeee eeeeeeeeee eee eeee eeeeeee ee eeee eee eeeeeeeeeeeee eeeee eeeeeeeeee ‌88‌ (e = 8) eeeeeeeeeeee eeee eeeeeeeeeee eeeeeee ‌88‌ (e = 8), eeeeeee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeee ee eee eeeeeee eeee e eeeeeeeeee-8-ee eeeeeeeeeee ‌88‌ (e = 8) eeeee eee α,β-eeeeeeeeeee eeeeeee ‌88‌ (e = 8) ee eee eeeee eeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee e Meeeeee Meeee ee e Meeeeeee β ee e Meeeeeee Meeee[‌888‌]

Meeeeeeeeeeee ee eee eeeeee eeeeeeeee eeeee eeeee ‌88‌ (‌Meeeee 88‌), eeeee eee eee eeee eeeeeee eeeee, eeeeeee eeeeeeeee ee eee 8M-eeeeeeee-8-eeeeeeeeeeeeeee eeeeeeeeee ‌88‌ eeee eeeeeeeeeee eeeeeee eeeee eeeeeeee eeeeeeeeee eeeee eee eeeeeeeeeeeee eeeee eeeee ‌88‌ ee 88% eeeeeee eeeee, eeeeeee eee eeeeeeeeeeeee eeeee eee eee eeeeeeeeeeeeeeeeeeee eeeeeeeeee ‌88‌ eeeee e 88% eeeee ee eee eeee eeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeee ee Meeeeeeeee ee Meeeeeeeeeeee eee 8M-Meeeeeee-8-eeeeeeeeeeeeeee eee Meeeeeeeeeeeeeeeeeee eeeeeeeeeee[‌888‌]

Meeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeee ee eeeeeeeee eeeeeeee ‌88‌ eee eeeee 8M-eeeeeeee-8-eeeeeeeeeeeeeee eeeeeeeeeee ‌88‌ ee eeee eeeeeeee ‌88‌ eee eeeee ee ‌Meeeee 88‌.

‌Meeeee 88‌ Meeeeeee Meeeeeee ee Meeeeeeeeeeee ee Meeeeeeee Meeeeeee eee Meeee 8M-Meeeeeee-8-eeeeeeeeeeeeeee Meeeeeeeeee[‌888‌,‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

M8	Meeeeeeeeeeeee Meeeeeeeeee	Meeee (%) ee ‌88‌	Meeeeeeee Meeeeeeeee	Meeee (%) ee ‌88‌	Mee
	MMMM, MMMM, MMM, ee	88	Me8MeM (8 eeeee), MMMM (8.8 eeeee), eeeeeee, eeeeee, 8 e	88	[‌888‌]
	MMMM, MM8Me8, ee	88	Me8MeM (8.8 eeeee), MMMM (8.88 eeeee), eeeeeee, eeeeee, 8 e	88	[‌888‌]
	MMMM, MMM, ee	88	Me8MeM (8 eeeee), MMMM (8.8 eeeee), eeeeeee, eeeeee, 8 eee	88	[‌888‌]
	MMMM, 8,8-eeeeeeeeeeeeee, 88°M	88	Me8MeM (8.8 eeeee), eeeeeee, eeeeee, 8.8 e	88	[‌888‌]
	MMMM (8 eeeee), MMMM (8.8 eeeee), MM8Me8, ee, 88 e	88e	Me8MeM (8 eeeee), MMMM (eee.), eeeeeee, 88°M, 8 e	88e	[‌888‌]
	MMMM, eeeeeee/eeeeeeee, (8:8), 88°M, 88 e	88	Me8MeM, eeeeeee, eeeeee	88	[‌888‌]

e MMMM = 8,8′-eeeeeeeeeeeeeeeeeeeeeee.

e Mee eeeeeeeee eeeeeee eeeeee ee eee eeeeeeeee eeeeeeeeeee eee eeeeeee.

Me eeee eeeee, eee eeeeeeee ee eeeeeeee ee eeeee eeeeeeeee eeeeeeee eeee 8,8′-eeeeeeeeeeeeeeeeeeeeeee eeeee ee eee eeeeeeeeeee ee eee eeeeeee eeeee ee ee eeeeeeee-8-ee eeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8ξ)-8-Meeee-8,8:8,8-ee-M-eeeeeeeeeeeeee-α-e-eeee-eeeeeeeeeeee (‌88‌):[‌888‌]

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

Meeee 8,8′-eeeeeeeeeeeeeeeeeeeeeee (8 eeee) eee eeeee ee e eeee ee eeeeeeeee eeeee eeeeeeeeee ‌88‌ (8 eeee) ee MMM ee 8,8-eeeeeeeeeeeeee (88 eM), eee eee eeeeeee eee eeeeeeee eeeee M8 eeeee eee eeeeeeee eeeeeeee eee eeeeeeee (MMM, 8–8 e). Mee eeeeeee eee eeee eeeeee eee eeeeeeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeeeeeeee ‌88‌; eeeee: 88%.

M eeee ee eeeeeeeeeeee ‌88‌ (8 eeee) ee eeeeeee (88 eM) eee eeeee eeeeeeee eeee 88 eee ee e eeeeeeeee eeeeeee ee Me8MeM (8.8 eeee) eee eeeeeee (888 eM) eeeee M8, eee eee eeeeeee eee eeeeeeee eeeee eee eeeeeeee eeeeeeee eee eeeeeeee (MMM, 8–8 e). Mee eeeeeee eee eeee eeeeee eee eee eeeeeee eee eeeeeeeeee. Mee eeeeeee eee eeeeeeeee eeee eee MeMM (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee eeeeee (8 × 88 eM), eee eee MeMM eeeee eee eeeeeeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.

(8M,8eM,8M,8eM)-8-eeee-Meeeee-8e-eeeeeeeeeeeeeee-8M-eeeee-8-ee Meeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

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

8,8′-Meeeeeeeeeeeeeeeeeeeeee (888 ee, 8.88 eeee) eee eeeee ee e eeee ee (8M,8eM,8M,8M,8eM)-8-eeee-eeeeee-8-eeeeeee-8e-eeeeeeeeeeeeeee-8M-eeeee-8-ee eeeeeee (888 ee, 8.88 eeee) ee MMM (88 eM), eee eee eeeeeee eee eeeeeeee eee 8 e, eeeeee, eee eeee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) ee eeee eee eeeeeeeeeeeee ‌88‌; eeeee: 888 ee (88%).

M eeee ee eeeeeeeeeeeee ‌88‌ (888 ee, 8.88 eeee) ee eeeeeee (88 eM) eeeeeeeeee MMMM (88 ee, 8.88 eeee) eee eeeee eeee 8 e ee e eeeeeeeee eeeeeee ee Me8MeM (8.88 eM, 8.88 eeee) eee eeeeeee (88 eM) eeeee eeeee. Mee eeeeeeee eee eeeeeeeee eeeee e eeeeeee eeee eee e Meeeee eeeeeee eeeeeeee eeeeeee eee eeeeee ee eee eee ee eee eeeeeeeee eee eeeeeeee eeeee ee eee eeeeeee ee eee eeee. Mee eeeeeee eee eeee eeeeeeee eee e eeeeeee 8 e eee eee eeeee eee 88 e. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee ee MeMMe/eeeeeee 8:8); eeeee: 888 ee (88%).

References

Meeeeee Meeeeeeeeee

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