Effect of substituents on the thermal decomposition ...

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Title Effect of substituents on the thermal decomposition of diazirines: Experimental and computational studies
Author(s) Michael T. H. Liu, Y. K. Choe, M. Kimura, K. Kobayashi, S. Nagase, T. Wakahara, Y. Niino, M. O. Ishitsuka, Y. Maeda, T. Akasaka
Journal Journal of Organic Chemistry
Date 2003
Volume 68
Issue 19
Start page 7471
End page 7478
Abstract The thermal decomposition of phenylehlorodiazirine (1), phenyl-n-butyldiazirine (2), and 2-adamantane-2,3'-[3H] diazirine (3) has been studied in solution in the presence Of C-60. The C-60 probe technique indicates that in the decomposition diazirine 1 yielded exclusively phenylchlorocarbene, diazirine 2 yielded mainly a diazo intermediate, and diazirine 3 yielded a mixture of carbene and diazo compound. In the case of diazirine 2, 13% of (E)-1-phenyl-1-pentene resulted from the direct thermal rearrangement of diazirine without the participation of a carbene. As well, the thermal decomposition of these diazirines has been studied theoretically with ab initio and density functional methods. The experimental results are broadly in agreement with the theoretical predictions. The calculations further indicate that the rebound reaction between carbene and molecular nitrogen leading to the formation of a diazo intermediate is an important reaction in the gas-phase decomposition of diazirine.

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