Part I. Thermal "ene" Reactions of Cyclopropenes With Classical Eneophiles. Part Ii. Generation And Rearrangement of Cyclopropenyl Carbinyl Anions

Cover Part I. Thermal "ene" Reactions of Cyclopropenes With Classical Eneophiles. Part Ii. Generation And Rearrangement of Cyclopropenyl Carbinyl Anions

Galley, Richard Allen

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The residue (0.466 g, 66%) was dissolved in hot chloroform-petroleum ether and cooled to room temperature. The product was collected on a filter, washed with cold petroleum ether and air dried, yielding E , Z-l , 4 , 5-triphenyl-2 , 4-pentadienone (84) (0.135 g, 22%) as yellow needles, mp 132-134°. The mother liguor was evaporated and the residue dissolved in hot petroleum ether. The solution was chilled and the pre- 251 cipitate collected on a filter, washed with cold petroleum ether and air d...ried. E ,E , 1 , 4 , 5-triphenyl-2 , 4-pentadienone (85) (0.252 g, 41%) as yellow needles, mp 80-32°.
Anal. Calcd. for C„ H 10 0: C, 89.00; H, 5.84.
Found: C, 8 9.11; H, 5.84.
The nmr spectrum (CDC1 ) showed a multiplet at £7.95- 7.70 (2H) , a multiplet at 7.55-7.30 (13H), a doublet for H 3 at 8.15 (1H, J = 15.0 Hz), a singlet for H 5 at 7.00 (1H) and a doublet for H at 6.58 (1H, J = 15.0 Hz) .
The infrared spectrum (KBr) showed carbon-hydrogen stretching at 2920 (w) , carbonyl stretching at 1645 (s) and olefinic stretching at 1530 (s) along with other ab- sorptions at 1435 (m) , 1278 (s), 1215 (s), 1020 (s) , 930 (m) , 880 (m) , 791 (w) , 778 (m) , 763 (m) , 746 (m) , 708 (s) and 698 (s) cm The mass spectrum showed a prominent molecular ion at m/e 310 (82%) along with other abundant fragments at m/e 233 (60%), 206 (16%), 205 (base peak), 204 (27%), 203 (24%), 202 (18%), 178 (9%), 105 (77%) and 77 (50%).

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