Acid-Catalyzed Intermolecular Rearrangement of N-Chlorocarbazole

Michael de Rosa; P. Andres Quesada; David J. Dodsworth

doi:10.1021/jo00378a002

Acid-Catalyzed Intermolecular Rearrangement of N-Chlorocarbazole

Michael de Rosa
, P. Andres Quesada
, David J. Dodsworth

Penn State Brandywine

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The chlorination of carbazole with sodium hypochlorite in CH₂Cl₂, CHCl₃, or CCl₄gave N-chlorocarbazole in 63-95% yield. It rearranged in refluxing methanol to give carbazole, 3-chlorocarbazole, 1-chlorocarbazole, 3,6-dichlorocarbazole, and 1,6-dichlorocarbazole. These chlorocarbazoles were formed in an acid-catalyzed intermolecular reaction. In the presence of potassium carbonate dechlorination of N-chlorocarbazole was observed. No evidence for an intramolecular rearrangement was found.

Original language	English (US)
Pages (from-to)	173-175
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	52
Issue number	2
DOIs	https://doi.org/10.1021/jo00378a002
State	Published - Jan 1 1987

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00378a002

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title = "Acid-Catalyzed Intermolecular Rearrangement of N-Chlorocarbazole",

abstract = "The chlorination of carbazole with sodium hypochlorite in CH2Cl2, CHCl3, or CCl4gave N-chlorocarbazole in 63-95\% yield. It rearranged in refluxing methanol to give carbazole, 3-chlorocarbazole, 1-chlorocarbazole, 3,6-dichlorocarbazole, and 1,6-dichlorocarbazole. These chlorocarbazoles were formed in an acid-catalyzed intermolecular reaction. In the presence of potassium carbonate dechlorination of N-chlorocarbazole was observed. No evidence for an intramolecular rearrangement was found.",

author = "\{de Rosa\}, Michael and \{Andres Quesada\}, P. and Dodsworth, \{David J.\}",

year = "1987",

month = jan,

day = "1",

doi = "10.1021/jo00378a002",

language = "English (US)",

volume = "52",

pages = "173--175",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

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T1 - Acid-Catalyzed Intermolecular Rearrangement of N-Chlorocarbazole

AU - de Rosa, Michael

AU - Andres Quesada, P.

AU - Dodsworth, David J.

PY - 1987/1/1

Y1 - 1987/1/1

N2 - The chlorination of carbazole with sodium hypochlorite in CH2Cl2, CHCl3, or CCl4gave N-chlorocarbazole in 63-95% yield. It rearranged in refluxing methanol to give carbazole, 3-chlorocarbazole, 1-chlorocarbazole, 3,6-dichlorocarbazole, and 1,6-dichlorocarbazole. These chlorocarbazoles were formed in an acid-catalyzed intermolecular reaction. In the presence of potassium carbonate dechlorination of N-chlorocarbazole was observed. No evidence for an intramolecular rearrangement was found.

AB - The chlorination of carbazole with sodium hypochlorite in CH2Cl2, CHCl3, or CCl4gave N-chlorocarbazole in 63-95% yield. It rearranged in refluxing methanol to give carbazole, 3-chlorocarbazole, 1-chlorocarbazole, 3,6-dichlorocarbazole, and 1,6-dichlorocarbazole. These chlorocarbazoles were formed in an acid-catalyzed intermolecular reaction. In the presence of potassium carbonate dechlorination of N-chlorocarbazole was observed. No evidence for an intramolecular rearrangement was found.

UR - https://www.scopus.com/pages/publications/0000254692

UR - https://www.scopus.com/pages/publications/0000254692#tab=citedBy

U2 - 10.1021/jo00378a002

DO - 10.1021/jo00378a002

M3 - Article

AN - SCOPUS:0000254692

SN - 0022-3263

VL - 52

SP - 173

EP - 175

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

Acid-Catalyzed Intermolecular Rearrangement of N-Chlorocarbazole

Abstract

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