Alkyl nitrite-metal halide deamination reactions. 7. Synthetic coupling of electrophilic bromination with substitutive deamination for selective synthesis of multiply brominated aromatic compounds from arylamines

Michael P. Doyle; Michael A. Van Lente; Rex Mowat; William F. Fobare

doi:10.1021/jo01301a004

Alkyl nitrite-metal halide deamination reactions. 7. Synthetic coupling of electrophilic bromination with substitutive deamination for selective synthesis of multiply brominated aromatic compounds from arylamines

The Journal of Organic Chemistry ◽

10.1021/jo01301a004 ◽

1980 ◽

Vol 45 (13) ◽

pp. 2570-2575 ◽

Cited By ~ 27

Author(s):

Michael P. Doyle ◽

Michael A. Van Lente ◽

Rex Mowat ◽

William F. Fobare

Keyword(s):

Aromatic Compounds ◽

Metal Halide ◽

Selective Synthesis ◽

Electrophilic Bromination ◽

Alkyl Nitrite

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ChemInform Abstract: ALKYL NITRITE-METAL HALIDE DEAMINATION REACTIONS. 7. SYNTHETIC COUPLING OF ELECTROPHILIC BROMINATION WITH SUBSTITUTIVE DEAMINATION FOR SELECTIVE SYNTHESIS OF MULTIPLY BROMINATED AROMATIC COMPOUNDS FROM ARYLAMINES

Chemischer Informationsdienst ◽

10.1002/chin.198047128 ◽

1980 ◽

Vol 11 (47) ◽

Author(s):

M. P. DOYLE ◽

M. A. VAN LENTE ◽

R. MOWAT ◽

W. F. FOBARE

Keyword(s):

Aromatic Compounds ◽

Metal Halide ◽

Selective Synthesis ◽

Electrophilic Bromination ◽

Alkyl Nitrite

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Alkyl nitrite-metal halide deamination reactions. 6. Direct synthesis of arenediazonium tetrafluoroborate salts from aromatic amines, tert-butyl nitrite, and boron trifluoride etherate in anhydrous media

The Journal of Organic Chemistry ◽

10.1021/jo01323a048 ◽

1979 ◽

Vol 44 (9) ◽

pp. 1572-1574 ◽

Cited By ~ 159

Author(s):

Michael P. Doyle ◽

William J. Bryker

Keyword(s):

Aromatic Amines ◽

Boron Trifluoride ◽

Direct Synthesis ◽

Boron Trifluoride Etherate ◽

Metal Halide ◽

Tert Butyl ◽

Alkyl Nitrite

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Alkyl nitrite-metal halide deamination reactions. 2. Substitutive deamination of arylamines by alkyl nitrites and copper(II) halides. A direct and remarkably efficient conversion of arylamines to aryl halides

The Journal of Organic Chemistry ◽

10.1021/jo00434a017 ◽

1977 ◽

Vol 42 (14) ◽

pp. 2426-2431 ◽

Cited By ~ 168

Author(s):

Michael P. Doyle ◽

Bernard Siegfried ◽

Joseph F. Dellaria

Keyword(s):

Metal Halide ◽

Aryl Halides ◽

Alkyl Nitrites ◽

Efficient Conversion ◽

Alkyl Nitrite

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Alkyl nitrite-metal halide deamination reactions. 3. Arylation of olefinic compounds in the deamination of arylamines by alkyl nitrites and copper(II) halides. A convenient and effective variation of the Meerwein arylation reaction

The Journal of Organic Chemistry ◽

10.1021/jo00434a018 ◽

1977 ◽

Vol 42 (14) ◽

pp. 2431-2436 ◽

Cited By ~ 53

Author(s):

Michael P. Doyle ◽

Bernard Siegfried ◽

Robert C. Elliott ◽

Joseph F. Dellaria

Keyword(s):

Metal Halide ◽

Alkyl Nitrites ◽

Alkyl Nitrite

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ChemInform Abstract: ALKYL NITRITE-METAL HALIDE DEAMINATION REACTIONS. PART IV. NITROSATIVE OXIDATION OF ARYLHYDRAZINES BY ALKYL NITRITES AND COPPER(II) HALIDES

Chemischer Informationsdienst ◽

10.1002/chin.197745203 ◽

1977 ◽

Vol 8 (45) ◽

pp. no-no

Author(s):

M. P. DOYLE ◽

B. SIEGFRIED ◽

W. F. FOBARE

Keyword(s):

Metal Halide ◽

Alkyl Nitrites ◽

Alkyl Nitrite

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Electrophilic bromination of gaseous aromatic compounds: Mechanism and linear free energy effects on reaction rates

Organic Mass Spectrometry ◽

10.1002/oms.1210281105 ◽

1993 ◽

Vol 28 (11) ◽

pp. 1313-1322 ◽

Cited By ~ 10

Author(s):

Olga Bortolini ◽

Sheng Sheng Yang ◽

R. G. Cooks

Keyword(s):

Free Energy ◽

Aromatic Compounds ◽

Reaction Rates ◽

Linear Free Energy ◽

Electrophilic Bromination

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ChemInform Abstract: ALKYL NITRITE-METAL HALIDE DEAMINATION REACTIONS. 3. ARYLATION OF OLEFINIC COMPOUNDS IN THE DEAMINATION OF ARYLAMINES BY ALKYL NITRITES AND COPPER(II) HALIDES. A CONVENIENT AND EFFECTIVE VARIATION OF THE MEERWEIN ARYLATION REACTION

Chemischer Informationsdienst ◽

10.1002/chin.197743149 ◽

1977 ◽

Vol 8 (43) ◽

pp. no-no

Author(s):

M. P. DOYLE ◽

B. SIEGFRIED ◽

R. C. ELLIOTT ◽

J. F. JUN. DELLARIA

Keyword(s):

Metal Halide ◽

Alkyl Nitrites ◽

Alkyl Nitrite

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Indirect electrochemical side-chain oxidation of alkyl aromatic compounds - selective synthesis of methyl benzoates or ortho-benzoic acid trimethylesters

Tetrahedron ◽

10.1016/s0040-4020(01)87454-8 ◽

1986 ◽

Vol 42 (2) ◽

pp. 553-560 ◽

Cited By ~ 28

Author(s):

Karl-Heinz Grosse Brinkhaus ◽

Eberhard Steckhan ◽

Dieter Degner

Keyword(s):

Benzoic Acid ◽

Aromatic Compounds ◽

Side Chain ◽

Selective Synthesis ◽

Chain Oxidation

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ChemInform Abstract: ALKYL NITRITE-METAL HALIDE DEAMINATION REACTIONS. 2. SUBSTITUTIVE DEAMINATION N OF ARYLAMINES BY ALKYL NITRITES AND COPPER(II) HALIDES. A DIRECT AND REMARKABLY EFFICIENT CONVERSION OF ARYLAMINES TO ARYL HALIDES

Chemischer Informationsdienst ◽

10.1002/chin.197743137 ◽

1977 ◽

Vol 8 (43) ◽

pp. no-no

Author(s):

M. P. DOYLE ◽

B. SIEGFRIED ◽

J. F. JUN. DELLARIA

Keyword(s):

Metal Halide ◽

Aryl Halides ◽

Alkyl Nitrites ◽

Efficient Conversion ◽

Alkyl Nitrite

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Alkyl nitrite-metal halide deamination reactions. 5. In situ generation of nitrosyl halides. Effective product control from nitrosyl chloride diazotization of primary aliphatic amines in N,N-dimethylformamide

The Journal of Organic Chemistry ◽

10.1021/jo00415a029 ◽

1978 ◽

Vol 43 (21) ◽

pp. 4120-4125 ◽

Cited By ~ 10

Author(s):

Michael P. Doyle ◽

Richard J. Bosch ◽

Paul G. Seites

Keyword(s):

Metal Halide ◽

Aliphatic Amines ◽

Nitrosyl Chloride ◽

In Situ Generation ◽

Effective Product ◽

Alkyl Nitrite ◽

Primary Aliphatic Amines ◽

Product Control

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