Conversion of -biphenylhydroxylamine to carbazole

Patrick, Timothy B.; Schield, John A.

doi:10.1016/s0040-4039(01)95831-9

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1973

2017

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Cited by 5 publications

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“…N-(2-Biphenyl)hydroxylamine (11) reacted with HF to yield a mixture containing carbazole (20), 2-amino-5-fluorobiphenyl, and 2,2'-azoxybiphenyl. 20 The production of carbazole suggests the intermediacy of an anilenium ion (A) which undergoes electrophilic cyclization with the ortho phenyl substituent.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of fluoroaromatic amines

Patrick¹,

Schield²,

Kirchner³

1974

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Synthesis of fluoroaromatic amines

Patrick¹,

Schield²,

Kirchner³

1974

J. Org. Chem.

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Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Berkowitz

McCombie

2017

Organic Reactions

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This chapter reviews in detail those reactions that form of a new pyrrole ring from vinyl, aryl, and heteroaryl azides via formal C–H insertion processes under thermal, photochemical, and metal‐catalyzed conditions. These reactions proceed via the intermediacy of vinyl or aryl nitrenes (or their metallonitrene equivalents) and generate a wide variety of pyrroles, indoles, carbazoles, and related systems. Methods for the synthesis of the starting azides are summarized, and a comprehensive survey of the cyclization processes is provided.

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