The Journal of Organic Chemistry

Cyclization of N-(2-biphenylyl) hydroxylamine derivatives to N-substituted carbazoles

FW Wassmundt, GT Babic

Index: Wassmundt, Frederick W.; Babic, Gary T. Journal of Organic Chemistry, 1982 , vol. 47, # 18 p. 3585 - 3587

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Citation Number: 5

Abstract

When lb was treated with P4OlO in refluxing benzene, a 70% yield of N-benzoylcarbazole (2b) was produced. The tosylhydroxylamine IC cyclized to N-tosylcarbazole (2c) in 55% yield under similar conditions. Hot polyphosphoric acid (PPA) was also effective: IC in hot PPA gave 2c in 46% yield. Hot PPA was not useful for the cyclization of 1 b since the product, N-benzoylcarbazole (2b), was unstable in hot PPA. A separate experiment ...