Naphthalene-1,4-imines deamination

In the 7-azabicyclo[2.2.1]heptadiene series there is as yet no instance known of aromatization by deamination such as occurs with some naphthalen-l,4-imine and anthracen-9,10-imine derivatives (see Sections III, H and IV, D). On the other hand, a close parallel exists between those reactions and some instances of aromatization of bicyclo[2.2.1] structures by loss of a heavier heteroatom from the 7-position, e.g., 70 71. 1,2,3,4,5-Pentaphenylphosphole reacts with dimethyl acetyl-... 

An interesting deamination of naphthalene- 1,4-imine 169 and anthracene-9,10-imine with PTC-generated dichlorocarbene was reported in 1981.265... 

Naphthalene is formed from the N-nitrosoimine 69 at 45°C via a cheletropic reaction.62 In some instances benzyne induces deamination of naphthalen-l,4-imines, since naphthalene was a by-product of the reaction of benzyne with N-methylpyrrole,63 and the naphthalene ester 79 is produced by reaction of 78 with benzyne.68 An indication of the fate of the extruded nitrogen-containing fragment is provided by the identification of N-methylcarbazole as a product of the reaction of 82 with benzyne. 

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