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  • preparation of 1 substituted 3 4 Dihydronaphthalene 2 carboxaldehyde n n dimethylhydrazones by palladium 0 coupling and their electrocyclic ring closure
    Tetrahedron, 1993
    Co-Authors: Thomas L Gilchrist, M A M Healy
    Abstract:

    Abstract 1-Bromo-3,4-Dihydronaphthalene-2-carboxaldehyde 2 has been converted by three methods, each involving halogen-metal exchange and palladium(0) catalysed cross coupling, into N,N-dimethylhydrazones of 1-aryl- and 1-vinyl-3,4-Dihydronaphthalene-2- carboxaldehydes. The N,N-dimethylhydrazone 10 of the aldehyde 2 undergoes efficient bromine-lithium exchange with butyllithium, as does 2-bromobenzaldehyde N,N-dimethylhydrazone 17. The dimethylhydrazones of 1-vinyl-3,4-Dihydronaphthalene-2-carboxaldehydes were not isolated by underwent electrocyclic ring closure followed by loss of dimethylamine in solution to give 5,6-dihydrobenz[f]isoquinolines. 1-Aryl-3,4-Dihydronaphthalene-2- carboxaldehyde N,N-dimethylhydrazones also cyclised in the same way when subjected to vapour phase pyrolysis.