Science of Synthesis

Sankararaman, S., Science of Synthesis, (2008) 43, 441.

Terminal and internal alkynes can be prepared by 1,2-elimination of heteroatom groups from an alkene. One such method is the reductive elimination of phosphates from vinyl sulfones ‌17‌ (‌Scheme 10‌).[‌23‌] Considering that the vinyl sulfone precursors ‌17‌ are conveniently prepared by the treatment of acid chlorides or esters with α-lithio sulfones (‌Scheme 10‌), this method offers a convenient route to alkynes ‌18‌. The reductive elimination reactions of the substrates ‌17‌ are carried out using either sodium in liquid ammonia or sodium amalgam in tetrahydrofuran.[‌23‌]

‌Meeeee 88‌ Meeeeeeee eee Meeeeeeee Meeeeeeeeee ee 8-Meeeeeeeeeeee Meeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

M8	M8	M8	Meeeee	Meeee (%) ee ‌88‌	Mee
Me	Me	MMe	M	88	[‌88‌]
Me	Me	MMe	M	88	[‌88‌]
8-eeeeeeeee	M	MMe	M	88	[‌88‌]
(MM8)88Me	eMe	MMe8	M	88	[‌88‌]
(MM8)88		MMe	M	88	[‌88‌]
	(MM8)8MM(MMe)Me	MMe	M	88	[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Meeeee M: Me ee eeee-eeeee, eeeee-eeeeee eeeee eeeeeeee eeee e M8 eeeee eee e eee eee eeeeeeeee eee eeeeee e eeee ee eee eeeee eeeeeeeee ‌88‌ ee MMM. MM8 eee eeeeeeeee eeee eee eeeee eee eeeee eeeeee ee eeeeeee eee Me eeeee eeee eeeeeeeeee eeeeee ee eee eeeeeeeeee eeeeeee eeee eeeee e eeee eeee eeeee eeeeeeeee. Meeee MM8Me ee MeMM eee eeeee ee eeeeee eee eeeeee eeeeeeeee, eee eee MM8 eee eeeeee eeeeeee ee eeeeeeeee eeeeeee eeeeeeee eeeeeee. Mee eeeeeee eee eeeeeeeeeee eeeeeee M8M eee eeeeeee ee Me8M. Mee eeeeeee eeeee eee eeeeee eeee 8 M MeMM (8 ×) eee eeeee. Meeeeee ee eee eeeeeee, eeeeeeee ee eeeeeeeeeeee eeeeeee e Meeeeee eeeeee ee eeeeeeeeeee eeeeeeee, eeeeeee eee eeeeee ‌88‌. Meee eeeeee ‌88‌ eee eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee eeee e Meeeeeeee eeee.

8-Meeeeeeeeeeeeeeee (‌88‌, M8 = 8-Meeeeeeee; M8 = M):[‌88‌]

Meeeee M: M eeeeeeeeee ee eee eeeee eeeeeeeee ‌88‌ (M8 = 8-eeeeeeeee; M8 = M; M8 = MMe; 8.8 e, 8.88 eeee) ee MMM (88 eM) eee MM8 (888 eM) eee eeeeeee eeeeeee eee eeeeeee eeee eeeee eeeeee ee eeeeeee eee Me eeeee e eeee eeee eee eeeeeeee. Meeee eeeeeeee ee eeeee MM8Me, eee eeeeeee eee eeeeee ee ee eeeeeeeee ee eee eeeeeee eeeeeeeee ee eeee e eeeeeeeee; eeeee: 8.88 e (88%).

References

Meeeeee Meeeeeeeeee

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