Science of Synthesis

Gandon, V.; Thorimbert, S.; Malacria, M., Science of Synthesis, (2009) 46, 197.

Terminal alkynes undergo homocoupling to form conjugated enynes in the presence of Wilkinson’s catalyst [chlorotris(triphenylphosphine)rhodium(I)]. Thus, when 3-(prop-2-ynyloxy)prop-1-ene (‌83‌) is treated with this catalyst and silver trifluoromethanesulfonate a [2 + 2 + 2] cycloaddition occurs that gives 6-[(allyloxy)methyl]-1,3,3a,4-tetrahydrobenzo[c]furan (‌84‌), together with a small amount of the acyclic dimer ‌85‌ (‌Scheme 30‌).[‌103‌]

‌Meeeee 88‌ Meeeeee-Meeeeeeee Meeeeeeeeeeeeeeee ee 8-(Meee-8-eeeeeee)eeee-8-eee[‌888‌]

Me eee eeeeeeee ee eeeeeeee eeeeeee eeeeeeeee, eeeeeeeeeeeee 8,8-eeeeee ‌88‌ eeeee eeee eeeeeee ee eeee eee eeeee eeeeeeeee-8,8-eeeeee ‌88‌ eee ‌88‌ eeee eeee e eeeeeeeeeee eeeeee ee eee eeee eeeeee (‌Meeeee 88‌).[‌88‌,‌88‌] Meee eeeeeeeeeeeeeeeeeeee eee ee eeeeeeee ee eeeee eee­eeeeee eeeee e eeeeee eeeeeeeeeee eeeeee (MeeMMMMM ee Mee-M-MMMM); eeeeeeeeee eeeeeeeeeeeeeeeeee eee eeee eeeeeeee eeee eeeeeeeeee eeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeeeeee [8 + 8 + 8] Meeeeeeeeeeeee eeeeeee 8,8-Meeeee eee Meeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

e Meeee eeeeee.

Meeeeeeee, eeeeee eeeeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeee eeeeeeeeeee eeeeeeeee ‌88‌ eee ‌88‌ eee eeeeeeee ee eeeee ee eeeeeee-eeeeeeeee [8 + 8 + 8] eeeeeeeeeeeeee eeeeeee 8,8-eeeeee ‌88‌ eee eeeeee eeeeeeee eeeeeeeee ‌88‌ eeee eeee e eeeeeeeee eeeee eeeeeee α ee eee eeeeeeee eeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeee [8 + 8 + 8] Meeeeeeeeeeeee eeeeeee 8,8-Meeeee eee α-Meeeeeeeeeeeee Meeeee Meeeeeee Meeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeee ee eeeeeeeee ‌88‌ eee ‌88‌ ee e >88:8 eeeee.

Meeeee eeeeeeeee eeeee ee e eeeeeee eeeeee eeee eeeeeeee 8,8-eee(eee-8-eeee)eeeeeeee (‌88‌) eee eeee e eeeeeee eeeeeeee {[Me(eee){(M)-M8-MMMMM}]MM8} ee eeeeee eee eeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌] Meeeee, ee eeeeee ee eeeee eeee, ee eeee, eeeeeee eeeeeeeee eee eeeeeeee eee eeee eeeeee eee eeeeeeeeeeeeeeee [8 + 8 + 8] eeeeeeeeeeeeee, ee eeee ee eeeee eeeeeee ee eeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeee [8 + 8 + 8] Meeeeeeeeeeeee eeeeeee Meeeeeee 8,8-Mee(eee-8-eeee)eeeeeeee eee Meeeee Meeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-Mee(eeeeeeeeeeeee)-8e-eeeeee-8-eeeeee-8-eeeee-8,8,8e,8-eeeeeeeeee-8M-eeeeeeeee (‌88‌, M8 = Me; M8 = Me; M8 = M8 = MM8MMe; M = MMe); Meeeeee Meeeeeeee:[‌88‌]

(M)-MeeMMMMM (8.8 ee, 8.888 eeee) eee [Me(eee)8]MM8 (8.8 ee, 8.888 eeee) eeee eeeeeee ee 8,8-eeeeeeeeeeeeee (8.88 eM) eeeee ee eeeeeeeeee ee eeeee ee ee eeeeeee e eeeeee eeee. 8,8-Meeeeeeeeeee-8-eee (88.8 ee, 8.88 eeee ee 888.8 ee, 8.88 eeee) eee eee eeeeeeeeeee ‌88‌ (M8 = Me; M8 = Me; M = MMe; 88 ee, 8.88 eeee) ee 8,8-eeeeeeeeeeeeee (8.88 eM) eeee eeeee ee eee eeee eee eee eeeeeee eee eeeeeeee eee 8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee (MMM) ee eeee eee eeeeee eeeeeeeeeee ee e eeeeeeeee eee; eeeee: 88 ee (88%); 88% ee [MMMM ee ee eeeee e eeeeee eeeeee (Meeeee Meeeeeeee MM-M: 8 × 888 ee, 888-ee MM eeeeeeee, eMeMM/eeeeee 8:8, eeee eeee 8.8 eM·eee−8); eM 8 eee eee eee eeeee eeeeeeee eee 88 eee eee eee eeeee eeeeee ‌88‌ (M8 = Me; M8 = Me; M8 = M8 = MM8MMe; M = MMe)].

Meeeeeee 8′,8′-Meeeeeee-8-eee-8′,8,8,8′-eeeeeeeeeeeeeee[eeeee-8,8′-eeeeee]-8′,8′(8′M)-eeeee­eeeeeeee [‌88‌, M8 = M8 = Me; M = M(MM8Me)8; M = M; e = 8]; Meeeeee Meeeeeeee:[‌88‌]

[Me(eee){(M)-Mee-MMMMM}]MM8 (8.8 ee, 8.888 eeee) eee 8-eeeeeeeeeeeeeeeeeeeee-8(8M)-eee (8.8 ee, 8.88 eeee) eeee eeeeeee ee 8,8-eeeeeeeeeeeeee (8.8 eM) ee 88°M ee eeee e eeeeee-eeeeee eeee. Meeeeeee 8,8-eee(eee-8-eeee)eeeeeeee [‌88‌, M8 = M8 = Me; M = M(MM8Me)8; 88.8 ee, 8.88 eeee] ee 8,8-eeeeeeeeeeeeee (8.8 eM) eee eeeee eeeeeeee eeee 88 eee ee eeee eeee eeeee ee eee eeeee eeeeeeeeee ee 88°M, eee eee eeeeeee eee eeeeeee eee 8 eee. Meeee eee eeeeeeee eee eeee, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeeee eeee eeeeeeee ee MMM [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee)/MeMMe 88:8] ee eeee eee eeeeeeeeeeee eeee eeeee eeeeeeee; eeeee: 88.8 ee (88%). Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee ee MMMM eeeeeeee eeeee e eeeeee eeeeee (Meeeee Meeeeeeee MM-M, eMeMM/eeeeee 8:8; eeee eeee: 8.8 eM·eee−8); eM 88 eee eee eee eeeee eeeeeeee, eee 8 eee eee eee eeeee eeeeee ‌88‌ [M8 = M8 = Me; M = M(MM8Me)8; M = M; e = 8].

References