Even though compound 6 is extremely sensitive towards air it is thermally very stable and melts without decomposition at 237 "C. An irreversible rearrangement or decomposition reaction only occurs at above 267 "C and is indicated by a change in color from red to yellow. We will next investigate whether compound 6 can participate in typical reactions for 1,3-dienes, especially cycloadditions of the Diels-Alder type.
Experimental SectionLithium (60 mg, 8.7 mmol) was added to a solution of 3 (700 mg, 0.81 mmol) in dimethoxyethane (30 mL) and the initially blue-green, later red, mixture was stirred for 2 h a t room temperature. After separation of insoluble materials, the remaining solution was cooled to -3O'C and treated with mesityl bromide (80 mg, 0.40 mmol). After the solution had been allowed to warm to room temperature, it was stirred for 16 h. The precipitated solid was filtered off and recrystallized from toluene to furnish 6 (280 mg, 53 % yield) as reddish brown crystals; m.p. 237-238°C; 'HNMR (Bruker AM300, [D,]benzene, 25'C): 6 = 0.16 (d, 3H, J = 6 . 6 H z ) , 0.24 (d, 3H, J = 6 . 5 H z ) , 0.34 (d, 3H, J = 6 . 5 H z ) , 0.45 (d, 3H, J=6.6Hz), 0.52 (d, 3H, J = 6 . 5 H z ) , 0.85 (d, 3H, J = 6 . 5 H z ) , 1.02 (d, 3H, J = 7 H z ) , 1.08 (d, 3H, J = 6 . 8 H z ) , 1.09 (d, 3H, J = 6 . 8 H z ) , 1.14 (d, 3H, J = 6 . 8 H z ) , 1.15 (d, 3H, J = 6 . 8 H z ) , 1.34 (d, 3H, J = 6 . 5 H z ) , 1.35 (d. 3H, J = 6 . 5 H z ) , 1.37 (d, 3H, J = 6 . 5 H z ) , 1.64 (d, 3H, J = 6 . 5 H z ) , 1.69 (d, 3H, J = 6.5 Hz), 1.78 (d, 3H, J = 6.6 Hz), 1.88 (d, 3H, J = 6.5 Hz), 2.55 (sept., 1 H, J=65Hz),2.64(sept., lH,J=6.5Hz),2.65(sept.,lH,J=6SHz),3.44(sept., 2H. J=6.5Hz),3,56(sept.,lH,J=6.8Hz),3.86(sept.,lH,J=6.5Hz),4.42 (sept., 1 H, J = 6."Si NMR (Bruker AMX300, [D,]benzene, 25°C): 6 = 52.3 (s), 89.5 (s); MS (CI, NH,): m/z (%): 1349 (4, MNH,'), 1332 (9, MH+); UV/Vis (THF): i.,,, (lge) = 392 (4.48). 518 (4.41) nm.