J . Am. Chem. SOC.1990, 112, 2407-2410 "C dec; 'H NMR 6 7.81-7.65 (m, 7 H), 7.48-7.42 (m, 5 H), 7.33-7.16 (m.19 H), 7.05 (d, 2 H, J = 8.3 Hz), 5.68 (s, 1 H); I3C NMR 146.5 (quaternary), 144.6 (quaternary), 144.4 (quaternary), 143.7 (quaternary), 141.5 (quaternary). 141.2 (quaternary), 133.3 (quaternary), 132.9 (quaternary), 132.1 (quaternary), 131.7 (quaternary), 131.2, 130.9, 129.5, 128.6, 128.33, 128.29, 128.0, 127.9, 127.8, 127.5, 127.2, 16.5, 126.4, 126.0, 125.97, 125.8, 125.6,64.7 (quaternary), 56.5 ppm; MS(C1) m / e 604 ( M + NH4*). Anal. Calcd for C46H34:C, 94.16; H, 5.84. Found: C, 94.10; H, 5.85. Reaction of 7a (Ai = 4-tert-Butylphenyl) with DABCO and Hg. A solution of the propyne 7a (56 mg, 0.115 mmol) in I O mL of dry, degassed T H F was treated with Hg metal (106 mg, 0.53 mmol) and DABCO (86 mg. 0.767 mmol). The mixture was heated in a sealed tube at 70 "C for 22 h. The tube was then opened and the mixture was filtered. By 'H NMR, the crude reaction showed no methine proton characteristic of rearranged dimer. Concentration in vacuo and column chromatography of the residue (flash silica gel; gradient, 2.5-50% benzene/hexane) gave 14.7 mg (30%) of bis[P-naphthyl(4-lerf-butylphenyl)methyl] peroxide: mp 181-183 "C dec; 'H NMR 6 7.74 (d, 1 H, J = 7.5 Hz), 7.60-7.58 (m,3 H), 7.39 (m, 2 H), 7.27 (dd, J = 8.7, 1.8 Hz), 7.21 (d, 4 H, J = 8.6 Hz), 7.15 (d, 4 H, J = 8.6 Hz), 1.30 (s, 18 H). Isomerization of Alkyne 7 to Propediene 5 with Alumina. Alkyne 7a ( 1 1 mg, 0.030 mmol) was added as a solid in one portion to 389 mg of basic alumina (Brockman activity I, further activated by heating at 400 "C at 0.05 mmHg for 24 h) suspended in 0.7 mL of dry toluene (or petroleum ether) at -20 O C . The resulting mixture was vigorously stirred at -20 OC for 25 min. By TLC, the alkyne was consumed and a slightly higher R,UV-active spot was present (10% benzene/hexane). Cold THF (
