The decomposition mechanism of 2-ethyl-hexylnitrate (2-EHN), an important additive to diesel fuel to improve the cetane number, was investigated in solution and in the gas phase. In trans-decalin as solvent, an activation barrier for the thermal decomposition of 39 kcal/mol was determined, and thus the decomposition is slow at temperatures below 100 • C. Under high pressure conditions (2.4 kbar) the decomposition rates decrease, in accordance with a radical mechanism. Flash vacuum pyrolysis with subsequent detection of the products via mass spectroscopy or matrix IR spectroscopy allows to identify NO 2 , formaldehyde, and several olefins as the major decomposition products. These data allow proposing a consistent mechanistic scheme for the 2-EHN decay.
and 5-azidobicyclo [2, 1,1]hexene (2b) rearrange cleanly at 30-50" to give exo-6methoxy-(lc) and 6-azidobicyclo[3,l,0]hexene (Id) respectively; reduction of (2b) below 0" proceeds with rearrangement to 5-aminobicyclo [3,1,0]hexene.
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