Why other benzene derivatives do not undergo nitrosationNitrosation of benzeneRegioselectivity of acid-catalyzed ring-opening of epoxidesNitrosation of benzeneAcidic nature of benzene and other alkenesNomenclature of benzene derivatives with two functional groupsWhy does selenophene not undergo aromatic substitution?Isocyanides undergo addition reactions, but cyanides do not. Why?Thermodynamic stability of benzene derivativesWhy does a Beckmann Rearrangement not occur in the in nitrosation of cyclohexanone?Why ammonium salts can not undergo substitutionDoes CF3COOH undergo decarboxylation ? Why or why not?
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Why other benzene derivatives do not undergo nitrosation
Nitrosation of benzeneRegioselectivity of acid-catalyzed ring-opening of epoxidesNitrosation of benzeneAcidic nature of benzene and other alkenesNomenclature of benzene derivatives with two functional groupsWhy does selenophene not undergo aromatic substitution?Isocyanides undergo addition reactions, but cyanides do not. Why?Thermodynamic stability of benzene derivativesWhy does a Beckmann Rearrangement not occur in the in nitrosation of cyclohexanone?Why ammonium salts can not undergo substitutionDoes CF3COOH undergo decarboxylation ? Why or why not?
$begingroup$
Solomon and Fryhle $11 th$ ed :
Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.
I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $ce-^+N=O$ for example with anisole.
Also it seems to contradict ron's answer
So which one is correct?
organic-chemistry amines
edited 18 hours ago
Avnish Kabaj
3,63831347
asked 22 hours ago
StarboyStarboy
405
$endgroup$
add a comment |
$begingroup$
Solomon and Fryhle $11 th$ ed :
Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.
I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $ce-^+N=O$ for example with anisole.
Also it seems to contradict ron's answer
So which one is correct?
organic-chemistry amines
edited 18 hours ago
Avnish Kabaj
3,63831347
asked 22 hours ago
StarboyStarboy
405
$endgroup$
$begingroup$
I don't see any contradiction.
$endgroup$
– Mithoron
8 hours ago
add a comment |
$begingroup$
Solomon and Fryhle $11 th$ ed :
Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.
I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $ce-^+N=O$ for example with anisole.
Also it seems to contradict ron's answer
So which one is correct?
organic-chemistry amines
edited 18 hours ago
Avnish Kabaj
3,63831347
asked 22 hours ago
StarboyStarboy
405
$endgroup$
Solomon and Fryhle $11 th$ ed :
Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.
I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $ce-^+N=O$ for example with anisole.
Also it seems to contradict ron's answer
So which one is correct?
organic-chemistry amines
organic-chemistry amines
edited 18 hours ago
Avnish Kabaj
3,63831347
asked 22 hours ago
StarboyStarboy
405
edited 18 hours ago
Avnish Kabaj
3,63831347
asked 22 hours ago
StarboyStarboy
405
edited 18 hours ago
Avnish Kabaj
3,63831347
edited 18 hours ago
Avnish Kabaj
3,63831347
edited 18 hours ago
Avnish Kabaj
3,63831347
3,63831347
asked 22 hours ago
StarboyStarboy
405
asked 22 hours ago
StarboyStarboy
405
asked 22 hours ago
StarboyStarboy
405
405
$begingroup$
I don't see any contradiction.
$endgroup$
– Mithoron
8 hours ago
add a comment |
$begingroup$
I don't see any contradiction.
$endgroup$
– Mithoron
8 hours ago
$begingroup$
I don't see any contradiction.
$endgroup$
– Mithoron
8 hours ago
$begingroup$
I don't see any contradiction.
$endgroup$
– Mithoron
8 hours ago
add a comment |
1 Answer
1
active
oldest
votes
$begingroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggests to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 19 hours ago
WaylanderWaylander
6,53411424
$endgroup$
add a comment |
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1 Answer
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active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
$begingroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggests to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 19 hours ago
WaylanderWaylander
6,53411424
$endgroup$
add a comment |
$begingroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggests to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 19 hours ago
WaylanderWaylander
6,53411424
$endgroup$
add a comment |
$begingroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggests to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 19 hours ago
WaylanderWaylander
6,53411424
$endgroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggests to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 19 hours ago
WaylanderWaylander
6,53411424
edited 13 hours ago
answered 19 hours ago
WaylanderWaylander
6,53411424
answered 19 hours ago
WaylanderWaylander
6,53411424
answered 19 hours ago
WaylanderWaylander
6,53411424
6,53411424
add a comment |
add a comment |
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$begingroup$
I don't see any contradiction.
$endgroup$
– Mithoron
8 hours ago