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Communication | Regular issue | Vol 6, No. 11, 1977, pp.1789-1792
Published online, 1st January, 1970
DOI: 10.3987/R-1977-11-1789
Studies with Reissert Compounds. Part VI. Change of Pathway Occasioned by Phase Transfer Catalysis: Suppression of N-Acyl Pseudo-base Formation in Favour of a Reissert Reaction

Barrie C. Uff* and Ronald S. Budhram

*Department of Chemistry, Loughborough University of Technology, Loughborough, Leicestershire, LE11 3TU, U.K.


Treatment of phthalazine with p-chlorobenzoyl chloride and potassium cyanide in a two-phase system gives an 1-acyl pseudo-base (3, R = 4-ClC6H4). Addition of a phase transfer catalyst to the medium changes the reaction pathway to give a Reissert compound (4, R = 4-ClC6H4) as major product with only a trace of N-acyl pseudo-base. The same change is observed with 5-nitroisoquinoline and a variety of acid chlorides. Inclusion of a phase transfer catalyst also increases the yields of Reissert compounds in reactions in which N-acyl pseudo-bases are not involved.