Science of Synthesis

Aggarwal, V. K.; Crimmin, M.; Riches, S., Science of Synthesis, (2008) 37, 353.

Sulfonium alkylides may be synthesized by the addition of a nucleophile to a vinylsulfonium salt {‌Scheme 54‌; see also Science of Synthesis, Vol. 27 [Heteroatom Analogues of Aldehydes and Ketones (Section ‌27.1.3.1.4‌27.1.3.1.4)]}.[‌159‌] If the nucleophile itself posses an electrophilic carbonyl group, an intramolecular epoxyannulation may be realized. This variation potentially allows a three-component coupling reaction.

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeee Meeeeeeee ee Meeeeeee ee e Meeeeeeeeee ee e Meeeeeeeeeeeee Meee[‌888‌]

Mee eee ee e eeeeeeee(eeeee)eeeeeeeee eeee ee ee eeeee eeeeeeeee ee eeeee eeeeeeeeeee, eee eeee eeeeeee eee eeeeeeeee eeee eee eeeeeeeeeee eeeeeee eeeeeeeeeeee ee eeeeeeeeee ee eeeeeeeeeeee eeeeeeee, eee eeee eeeeeee eee eeeeeeeee eeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeee eee eee eeeeeee e eeeeee eeeee ee eee eeeeeeeeeeeee eeeee(eeeeee)eeeeeeeee eeeeeeeee.[‌888‌] Me eeeeeee, eee eeeeeeee eeee eee eeeeeeee eeeeeee eeeeeeeeeeee ee eee eeeeee eeeeeeeee ee eee eeeeeeeee eeeeeeee ee eeeee eeeeeee eee eeeeeee e 8,8-eeeeee eeeee, eeeeeeee ee eeeeeeee ee eee eeeeeeeee eeeeeee. Meee eeeeeeee ee eeeeeeeeeeeee eeeeee ee eee eee eeeee eee eee eeee eeeeeee ee eee eeeeeeeee ee e eeeeee ee eeeeeeeeeeeee eee eeeeeeeeee (‌Meeeee 88‌).[‌88‌,‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeee ee Meeeeee Meeeeeeeeeee eeee Meeeeeeeeeeeee Meeee[‌88‌,‌888‌–‌888‌]

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

‌Meeeee 88‌ Meeeeeeeeeeeeee eeee e Meeeeeeeeeeeee Meee[‌888‌,‌888‌]

Me eeeeeeeeee eeeeeee ee eeeee eeeeeeeeeeeeeee eeeeeeeee eee eeee eeeeeeee ee Meeeeeee ee ee. eeeeeee eee eee ee eeeeee eeeeeee ‌88‌. Meee eeeeeeeeee eeeeeee ee eeeeeee eee ee e eeeeeeeeeeeee ee 8.888 M eee eee ee eeeeeee ee eee eeeeeeeee ee eeee eeee- eee eee-eeeeeeee eeeee eee eee ee eeee ee eeeeeeeee eeee eeeeeeeee eee eeeeeee eeee eeee ee eeeeeeeee eeeeee eee eeeeeeeee eeeeeeeeeeeeeeeeeeee (‌Meeeee 88‌). M eeeeeee eeeeeeee eeeee eeeeeeee eeeeeee ee eeeee ee eee eeeeee eeeeeee eee eeee eeee eeeeeeee eee eee eeeeeeeee ee eeeee-eeeeeeee eeeee eee eee eeee eeeeeee eeeeee e eeeeee eeeeeeeee ee eeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeee’e Meeeeeeeee Meeeeeeeeeeeeee eeee Meeeeeeeeeeeee Meeee Meeeeee eeee e Meeeee Meeeeee[‌888‌]

Meeeeeeee eeeeeeeee eee ee eeeeeeeeeee ee eee eeeeeeee ee e eeee eeeeeeeeeee ee e eeeeeeeeeeeeeeeeeee eeee.[‌888‌] Mee eeeeeeeeeeee eeeeee ee ee eeeeeeee, eeeeeeee, ee eeeeeee ee 8-eeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee ee eeeeeee eeeeeee ee eee eeeeeeeee ee e eeeeeeeee eeeeeeee eeeee eee eeeee ee eeee ee eeeeee eee eeeeeeeeeee ee e eeeeeeee eeeeeeee (‌Meeeee 88‌).[‌888‌] Mee eeeeeeee ee eeeeeeeeeee ee eee eeeeeeeeee ee eee eeeeeeeeeeee ‌88‌ ee eeeeeee e [8,8]-eeeeeeeeeee eeeeeeeeeeeee eee eeeeeee eeeeeee eeee eeeeeeeee ee eee eeeeeee eeee ee ‌88‌ eeeeeee e eeeeeeeeeee eeeeeeeeeeeee eeeee −88 °M. Mee eeeeeeee eeee eee eeeeeeee eeeeeee eeeeeeeeeeee (MeM−), ee eee eeeeee eeeeeeeee ee eee eeeeeeeee eeeeeeee ee eeeee eeeeeee eee eeeeeee e 8,8-eeeeee eeeee, eeeeeeee ee eeeeeeee ee eee eeeeeeeee eeeeeeeeeeee eeeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeee Meeeeeee Meeeeeeeee ee Meeeeeee ee e Meeeeeeeeee ee e Meeeeeeeeeeeeeeeeee Meee[‌888‌–‌888‌]

Mee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeee eeeeee ee ee eeeeeeee eeee eeee-8,8-eeeeeeeeeeeeeeeeeeeeeee eeee ‌88‌, eeeeee ee eee eeeeeeee ee e eeeeeeee ee eeee eeeeeeee eeee eeeeeeeeee eeeeeeee ee e eeeeeeee, eeeeee e eeeee-eeeeeeeee eeeeeeee eeeeeeeeeee eeeeeeeee (‌Meeeee 88‌).[‌888‌,‌888‌] Meeeeeeee eeeeeeeeeee eee eeee eeeeeeeeeeee eee e eeeeee ee eeeeeeee, eeeeeeeee, eee eeeeeeeeeeeeee eeeeeeeee. Meeeeee eee eee eeeeeeeee, eeeeeeeeee eeeeeeee eeeeeeeee eeee ee eeeeeeeeee ee eeeeeeeeeeee ee eee eeeee eee, ee eeeeeee, eeee eee eeeeeeee eeeeeee eeeeeee eeee eeeeeeee eee [8,8]-eeeeeeeeeee eeeeeeeeeeeee eeeeeee eeeeeee eeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee e Meeee Meeeeee eee e Meeee-Meeeeeeee Meeeeeee[‌888‌]

Mee eeeeeeee ee ee eeeeeee ee eeee-8,8-eeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee (‌88‌) eee ee eeeeeeee ee ee eeeeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeeee eeeeeeeee eeeeeeee.[‌888‌,‌888‌] Meee eeeeeeee eeeeee eeeeee eeeeee ee 8-eeeeeeeeee[8.8.8]eeee-8-eeee eee eeee eeeeeee eeeeee eeeeeee eee eeeeeeeeee eeeeeeeeeeeee eeeeeeee eeeeee ee eeeeeeee eeeeee eeee eee eeeeeeeeeeeeeeee eeeeeeeeee. Me eeeee eeeeeeee eee eee eee, eeee eee [8,8]-eeeeeeeeeee eeeeeeeeeeeee eeeeeee eeeeeee eeeeeeeeeee eee, ee eeeeeee, eeee eeeeeeee eeee eeee eeeeeeee eee eeeeeeee. Me eeee eeeee, eee eeeeeeee eeeeeeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeee eeee eee eeee eeeeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeeeeeeee ee Meeeeeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeee-8,8-eeeeeee-8M-eeeeeee[8,8-e]eeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8M-eeeeee-8-eeeeeeeeeeee (8 eeee) eee MeM (88% eeeeeeeeee ee eeeeeee eee, 8 eeee) eee eeeeeee ee eee MMM eeeee M8 ee 8 °M. Meeee 88 eee, eeeeeeee(eeeee)eeeeeeeee eeeeee (8 eeee) eee eeeee eee eeeeeee eee eeeeeee eee 88 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeee eeee eeeeeee ee eeeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee eee eeeeeeeeeeeeeeeee eeee eeeeeee ee e eeeee eeeee; eeeee: 88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.