Science of Synthesis

Sankararaman, S., Science of Synthesis, (2008) 43, 444.

A modification of the Corey–Fuchs synthesis has been reported in which the 1,1-dibromoalkene is directly converted into 1-bromoalkyne ‌23‌ by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethyl sulfoxide (‌Scheme 13‌).[‌27‌] This variation of the Corey–Fuchs methodology is very useful considering that 1-bromoalkynes are useful starting materials for the well-known Cadiot–Chodkiewicz coupling for the synthesis of diynes {see Science of Synthesis, Vol. 24 [Three Carbon—Heteroatom Bonds: Ketene Acetals and Yne—X Compounds (Section ‌24.4.1.2.1‌24.4.1.2.1)]}.

‌Meeeee 88‌ Meeeeeee Meeee–Meeee Meeeeeee eee eee Meeeeeeee ee 8-Meeeeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

Mee Meeee–Meeee eeeeeeeee ee eeeeeee eeee eeeeeeeee eeeeeeee eee eeeee. Mee eeeee eeee eeeeeeee eee eeeeeeeeee ee eee eeeeeeee eeee eee eeeeeeeeeeee eeeeeeeeee, eee ee eee eeeeee eeee eeeeeeeeeee eeeeee ee eeee eee eeeeee. M eee-eee Meeeee eeeeeeeee eee eee eeeeeeeee ee eeeeeeee eeeeeee eeee eeeeeeeee ee eeee eeeee eeeee (eeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee eeeeeee ‌88‌ ee eee eeeeeee (‌Meeeee 88‌; eee e eeeeeee eeeeee, eee eeee Meeeeee ‌88.8.8.8.8.8‌).[‌88‌] Meeeeeeee ee ee eeeeeeee eeee eeeeeeeeeee eeee ‌88‌, ee eee eeeeeeee ee eeeeee eeeeeeeee eeee-eeeeeeee, eeeeeeee eee eeeeeeeeeeeee eeeeeeee eeeeee ‌88‌ ee eeee ee eeeeeeeee eeeeee. Meee eeeeeeeee ee eeee eeeeeeee eeee eee Meeee–Meeee eeeeeeeee, eeeeeee ee eee eeeeeee ee eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeeee (eee MeMe8 eeee Me ee eeee) eeeeeeeee ee eeeeeeee ee eeeeeeeeeeeeeeeeee (ee Me) eee eeeeee eeeeeeeeeeee. Meee α,β-eeeeeeeeeee eeeeeeeee eee eeee ee eeee eeeeeeeee, eeeeeeeeeeeee ee eee eeeeee eeee eeee eee eeee eeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Mee-Mee Meeeee Meeeeeeeeee Meeeeeee eee Meeeee Meeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

M8MMM	Meeee (%)	Mee
(M)-MM=MMMe	88	[‌88‌]
8-Me8MM8M8	88	[‌88‌]
8-MeM8M8	88	[‌88‌]
	88	[‌88‌]
	88	[‌88‌]
	88	[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Me e 88 eM eeee ee eee eeeee eeeeeeeee ee MMMM eee eeeee e 8 M eeee ee MMM ee MMMM (88 eM, 88 eeee). Meeee eee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeeeeee eeee 8.8 M MMe. Meeee eeeeeeee eeeeeee eeeeee, eeeeeeeeee eeee MM8Me8, eee ee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee, eee eeeeeeeeeee eee eeeeeeee ee eeee eeee.

Meeeeeee Meeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Meeee ee eeeee eeeeeeeeee, (eeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee eeeeeee (‌88‌; 8 eeee) eee e-MeMM (8.8 eeee) eeee eeeeeeeee ee MMM (88 eM). Mee eeee eee eeeeeee eee e eee eeeeeee eee eee eeeeeeee (8 eeee) eee eeee eeeee. Meeee 88 eee, e-MeMM (88 eeee) eee eeeee ee ee. Mee eeee eee eeeeeeee eeee eee. eeeee (88 eM) eee eeeeeeeee eeee Me8M (88 eM). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee. Meeeeeeeeeeeeee eeeeeeeeeeee (eeeeee eee) eeeeeeee eee eeeeeeeeeeeee eeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.