The photochemistry of [p-(dimethylamino)phenyl]pentazole ( @entity34484 ) at 193 nm and in the near UV is reported, with emphasis on the nature of the final stable products. The (dimethylamino)phenyl azide ( @entity68384 ) is found as a major product in @entity15544 , but not in @entity1044 ( @entity17058 ). (In this paper the acronyms @entity34484 and @entity68384 refer to the para isomers.) The photochemistry of @entity68384 is also explored for comparison. The data obtained in MeCN solutions are consistent with the initial formation of the corresponding @entity68385 , but in DCM, different products are found, on the basis of NMR data. In the case of high reactant concentration in DCM (10(-2) M), quantitative conversion of @entity34484 and @entity68384 is observed, indicating a high quantum yield. In contrast, MeCN solutions react much more slowly. A radical-type chain reaction mechanism is proposed to account for this observation. At high dilution, @entity34484 is completely converted to products in both solvents. Possible mechanisms accounting for these results are discussed.

Solution Photochemistry of [p-(Dimethylamino)phenyl]pentazole ( XXXX ) at 193 and 300 nm.

@entity34484 :: ('MESH:C043060', 'Chemical') :: ['DMAPP'] @entity68385 :: ('MESH:C017621', 'Chemical') :: ['nitrene'] @entity1044 :: ('MESH:D008752', 'Chemical') :: ['dichloromethane'] @entity68384 :: ('MESH:C044974', 'Chemical') :: ['DMAPA'] @entity17058 :: ('CHEBI:15767', 'Chemical') :: ['DCM'] @entity15544 :: ('CHEBI:38472', 'Chemical') :: ['MeCN']
@entity34484 :: (MESH:C043060,Chemical) :: ['DMAPP']
