Add time:07/21/2019         Source:sciencedirect.com

Pyrolysis of 5H-dibenzo[a,d]cyclohepten-5-one oxime (8) and 10,11-dihydro-5H-dibenzo-[a,d]cyclohepten-5-one oxime (9) in a flow system (at 1.33 mbar and 650°C) were examined comparatively with pyrolysis of benzophenone oxime (1a) using GC/MS. The pyrolysis products of 8 were: 1-cyanophenanthrene (19), 3H-[3,4-a,5]isoxazolodibenzo[b,f]cycloheptene (20), dibenzosuberenone (12), dibenzosuberenone imine (23), anthracene (21) and phenanthrene (22). In the pyrolysis of 9, 1-cyano-9,10-dihydrophenanthrene (24), 4-cyano-9,10-dihydrophenanthrene (25), 3H-[3,4-a,5]isoxazolo-9,10-dihydrodibenzo[b,f]cycloheptene (26), dibenzosuberone (13) and dibenzosuberone imine (28) are accompanied by 21 and 22 as well as by dehydrogenation products 19 and 20. Pyrolysis of 1a at 800°C indicated formation of benzophenone (11) and benzophenone imine (18) along with the reported products benzonitrile (15), biphenyl (16), benzene (17) and 2-phenyl-benzoxazole (4a). The comparative reaction mechanisms for 1a, 8 and 9 are discussed. Pyrolytic formation of ketone imines and corresponding ketones seems to be a general reaction route (also proved for isodibenzosuberone oxime 10) in conditions favouring surface catalysis.

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