Science of Synthesis

Griesbeck, A. G.; Soldevilla, A., Science of Synthesis, (2008) 43, 376.

The Fritsch–Buttenberg–Wiechell rearrangement (see Houben–Weyl, Vol. 5/2a, p 214, and Section ‌43.8.2.1.5‌) provides an excellent method for the formation of diarylacetylenes ‌68‌ from 2,2-diaryl-1-haloalkenes ‌67‌ by treatment with alkoxides or alkyllithium reagents (‌Scheme 38‌).[‌120‌] The reversible formation of a (halogen, metal)–alkylidene-carbenoid, which collapses with 1,2-aryl migration, is postulated. Incorporation of the triple bond into a larger ring system can be achieved by this process.[‌121‌]

‌Meeeee 88‌ Meeeeee–Meeeeeeeee–Meeeeeee Meeeeeeeeeeee ee 8-Meeeeeeeeeeee[‌888‌]

Meee eeeeeeeeeeeee eee eeee eeee eeeeeee ee eee eeeeeeeee eeeeee eeeee eeeeeeeeeee eeeeeeeeee eeee eeeeeeeeee,[‌888‌] eee eee 8-eeee-8-eeeeeee-eeeeeeeeeee eeeeeeeeee.[‌888‌] Meeeeeeeeee ee eee Meeee–Meeee eeeeeeeee eee eeeeeeeee {eee Meeeeee ee Meeeeeeee, Mee. 88 [Meeeeeeee (Meeeeee ‌88.8.88.8.8‌88.8.88.8.8)]}, eeeeeee eee eeeeeeeee eeee 8,8-eeeeeeeeeeeeee eeee eeeeeeeee eeee eeeeeeeee eeee eeeeeeeeeeee eeee eeeeeee eeeeeeeeee, eeeee eee ee eeeeeeeeee ee eeeeeee eeee eeeee eeeeeeeeeeeee.[‌888‌] ‌Meeeee 88‌ eeeee eeeeeeee ee eee eee ee eeee eeeeee: 8,8-eeeeeeeeeeeee ‌88‌ eeeee eeeeeeeee ‌88‌ ee eeeeeeee ee eee eeeeeee eeeeeeeee eeee ee eeeeeeee, ee eeeeeeee ‌88‌ ee Meeeeee eeeeeeee eeeeeeee eeee ee eeeeeeeee.

‌Meeeee 88‌ Meeeeee–Meeeeeeeee–Meeeeeee Meeeeeeeeeeee ee 8,8-Meeeeeeeeeeeee, Meeeeeee ee Meeeeeee eeee ee Meeeeeeeeee, ee Meeeeee Meeee-Meeeeeee Meeeeeee eeee e Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee-8,8-eeee-8-eee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

(8,8-Meeeeeeeee-8-ee-8-ee-8-ee)eeeeeee (‌88‌; 8.8–8.8 eeee) eee eeeeeeeee ee eeeeeee (8 eM). Mee eeee eee eeeeeee eeee eeeeeee (88 eM) eee eeeeee ee −88°M eeeee eeeee, eee 8.8 ee 8.8 M MeMe ee eeeeeee (8.8 eeeee) eee eeeee ee eeeeeee ee eee eeeeeee eeee eeee ee. 8 eee. Mee eeeeeee eee eeeeeee ee eeee eeeeee ee 8°M eee eeeeeeee ee −88°M, eee eeeee Me8M (88 eM) eee eeee eee eeeeeeee (8.8–8.8 eeeee), eeeeeeeee ee Me8M (8 eM), eeee eeeee eee eeeeeee. Mee eeeeeee eee eeeeeee ee eeee eeeeee ee ee eee eeeeeee eeeeeeeee. Mee. ee MM8Me (88 eM) eee Me8M (88 eM) eeee eeeee, eee eee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee eee. ee MeMe (8 × 88 eM), eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).

(8-Meeeeeeeee-8,8-eeeeee)eeeeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

(8,8-Meeeeeeeee-8-ee-8-ee-8-ee)eeeeeee (‌88‌; 8.8 eeee) ee eeeeeee (88 eM) eee eeeeee ee −88°M eeeee M8. 8.8 M MeMe ee eeeeeee (8.88 eM, 8.8 eeee) eee eeeee ee eee eeeeeee eeee ee eeeeeee eeee ee. 8 eee. Mee eeeeeee eee eeeeeee ee eeee eeeeee ee −88°M eee eeeeeeee ee −88°M, eee 8.88 M MeMe8 ee MMM (8.8 eM, 8.8 eeee) eee eeeee ee eeeeeee eeee ee. 8 eee. Mee eeeeeee eee eeeeeee ee eeee eeeeee ee 8°M, eee eeeeeeeee (8.8 eeee) eee Me(MMe8)8 (88 ee, 8.888 eeee) eeee eeeee eeeeeeee eeeee e eeee ee M8, eee eee eeeeeee eee eeeeee ee 88°M eee 88 e. Mee eeeeeee eee eeeeeee ee eeee, eee eeeeeeee eeeeeee e Meeeee eeeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MM8Me8).

References

Meeeeee Meeeeeeeeee

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