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Pyrolysis and Isomerization of Quadricyclane, Norbornadiene, and Toluene Zhi Li and Scott L. Anderson*
 

Summary: Pyrolysis and Isomerization of Quadricyclane, Norbornadiene, and Toluene
Zhi Li and Scott L. Anderson*
Department of Chemistry, UniVersity of Utah, Salt Lake City, Utah 84112
ReceiVed: July 13, 1998
Pyrolysis and isomerization of the C7H8 isomers quadricyclane, norbornadiene, cycloheptatriene, and toluene
have been studied in a micro-flow tube reactor with detection/isomer identification by guided-ion beam tandem
mass spectrometry. The methodology permits pyrolysis studies with product isomer identification with samples
of only a few milligrams. The samples are premixed with buffer gas and then passed through a temperature-
controlled flow tube reactor with millisecond residence time. The sample/pyrolysis products exiting the flow
tube are ionized by methane chemical ionization (CI), and both CI mass spectra and low-energy collision-
induced dissociation were used to determine the composition. For the experimental residence time, toluene
and cycloheptatriene are stable over the 298-998 K temperature range. Decomposition of norbornadiene
sets in at 600 K. The dominant decomposition processes are acetylene elimination via a retro-Diels-Alder
reaction and isomerization to toluene. Quadricyclane begins to decompose at 500 K, and the dominant
decomposition processes are the acetylene elimination and isomerization to toluene, with a small amount of
norbornadiene production. The results are discussed in relation to previous studies at lower temperatures/
longer times.
I. Introduction
Strained hydrocarbons, such as cubane or quadricyclane, are
an interesting class of molecules, both from a fundamental

  

Source: Anderson, Scott L. - Department of Chemistry, University of Utah

 

Collections: Energy Storage, Conversion and Utilization; Materials Science; Chemistry