1. Procedure The pyrolysis apparatus consisted of a quartz tube, 40 cm long and 0.8 cm in diameter. An appendage tube, covered with a septum, protruded at a 45º angle above the sample well and was located 7 cm after the inlet of the tube. This tube provided access to the well for introduction of the sample. The outlet of the pyrolysis tube led into a cooled glass coil where condensation of pyrolysate occurred. An acetone bubbler was placed at the end of the coils where the highly volatile products were collected. The appropriate coolant, dry-ice slush or liquid nitrogen, was chosen according to the condensation temperature of the inert gas used, either argon or helium. The inert gas was passed through the apparatus at 10-50 ml min -1 in various trials. In some trials, 0.1 g of nickel powder was spread along the bottom of the pyrolysis zone, 5-8 cm from the outlet of the tube, to serve as a catalyst. Approximately 1 g of a mixture of naphthalene and isoquinoline was placed into the sample well. A heating tape, enveloping the sample well and the first 33 cm of the pyrolysis tube, was used to vaporize the sample. A propane-oxygen torch heated 5 cm of the pyrolysis zone at a temperature of 1000-1200 ºC during multiple trials. These temperatures were measured using a type K thermocouple enclosed in a quartz sheath to simulate the effects of uniform heat transfer by black body radiation. Pyrolysis occurred over a period of twenty to thirty minutes. After cooling, the products were removed from the pyrolysis tube and glass coil by ultrasonication with acetone. This slurry was filtered using a Buchner funnel and the insoluble material was washed thoroughly with more acetone. The filter paper was then folded, placed into a test tube, and soaked in carbon disulfide to dissolve the fullerenes. After ultrasonication for at least one hour, the sample was filtered using glass wool. The filtrate was collected and concentrated under a stream of nitrogen. The sample was submitted for mass spectrometry using the chemical ionization technique. When mass spectral analysis suggested the presence of hydrogenated fullerenes in the sample, an attempt was made to dehydrogenate them. In 1990, Haufler et. al. reported that [60]fullerene could undergo Birch reduction to form C 60 H 36 [9]. This reaction was found to be fully reversible when the hydrogenated fullerenes, dissolved in toluene, were refluxed with 2,3-dichloro-5,6-dicyano-1,4- benzoquinone (DDQ). After the sample was filtered and the carbon disulfide was removed, the fullerenes were dissolved in 20-30 ml of toluene, depending on the amount of product. This solution was then refluxed with 0.25-1.0 g of DDQ for one to two hours. Stirring prevented a residue from accumulating on the sides of the RB flask during reflux. As the reaction progressed, small aliquots were taken at various time intervals to determine the extent of dehydrogenation. These aliquots were then submitted for mass spectroscopic analysis using the aforementioned technique.