Oxidative N−N Bond Formation Versus the Curtius Rearrangement

to related objects

Abstract: The oxidative formation of N−N bonds from primary amides has been recently reported and then retracted in the journal Nature Communications by Kathiravan, Nicholls, and co‐authors, utilizing a hypervalent iodane reagent. Unfortunately, the authors failed to recognize the Curtius reaction taking place under the described reaction conditions. Thus, the claimed N−N coupling products were not formed. Instead, the Curtius rearrangement urea coupling products were obtained. We demonstrate this herein by means of NMR and x‐ray analysis, as well as with the support of an alternative synthetic route.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Oxidative N−N Bond Formation Versus the Curtius Rearrangement ; volume:30 ; number:53 ; year:2024 ; extent:3
Chemistry - a European journal ; 30, Heft 53 (2024) (gesamt 3)

Creator: Hohenadel, Melissa
Ebel, Ben
Oppel, Iris M.
Patureau, Frederic W.

DOI: 10.1002/chem.202402355

URN: urn:nbn:de:101:1-2409271423348.055540894742

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:33 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Show original at data provider

Associated

Hohenadel, Melissa
Ebel, Ben
Oppel, Iris M.
Patureau, Frederic W.

Other Objects (12)

Oxidative N–N Bond Formation Versus the Curtius Rearrangement

Oxidative N–N Bond Formation Versus the Curtius Rearrangement

Oxidative Rearrangement of Tertiary Propargylic Alcohols

Oxidative Rearrangement of Tertiary Propargylic Alcohols

Enzymatic spiroketal formation via oxidative rearrangement of pentangular polyketides

Enzymatic spiroketal formation via oxidative rearrangement of pentangular polyketides

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Oxidative rearrangement of (+)-sesamin by CYP92B14 co-generates twin dietary lignans in sesame

Oxidative rearrangement of (+)-sesamin by CYP92B14 co-generates twin dietary lignans in sesame

A single diiron enzyme catalyses the oxidative rearrangement of tryptophan to indole nitrile

A single diiron enzyme catalyses the oxidative rearrangement of tryptophan to indole nitrile

Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

Development of new chemical oxidative, step and atom efficient C-N and N-N bond forming coupling reactions

Development of new chemical oxidative, step and atom efficient C-N and N-N bond forming coupling reactions

Genome rearrangement algorithms

Hochschulschrift

Genome rearrangement algorithms

Oxidative N–N Bond Formation Versus the Curtius Rearrangement

Oxidative N–N Bond Formation Versus the Curtius Rearrangement

Oxidative Rearrangement of Tertiary Propargylic Alcohols

Oxidative Rearrangement of Tertiary Propargylic Alcohols

Enzymatic spiroketal formation via oxidative rearrangement of pentangular polyketides

Enzymatic spiroketal formation via oxidative rearrangement of pentangular polyketides

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Oxidative rearrangement of (+)-sesamin by CYP92B14 co-generates twin dietary lignans in sesame

Oxidative rearrangement of (+)-sesamin by CYP92B14 co-generates twin dietary lignans in sesame

A single diiron enzyme catalyses the oxidative rearrangement of tryptophan to indole nitrile

A single diiron enzyme catalyses the oxidative rearrangement of tryptophan to indole nitrile

Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

Development of new chemical oxidative, step and atom efficient C-N and N-N bond forming coupling reactions

Development of new chemical oxidative, step and atom efficient C-N and N-N bond forming coupling reactions

Genome rearrangement algorithms

Hochschulschrift

Genome rearrangement algorithms

Oxidative N–N Bond Formation Versus the Curtius Rearrangement

Oxidative N–N Bond Formation Versus the Curtius Rearrangement

Oxidative Rearrangement of Tertiary Propargylic Alcohols

Oxidative Rearrangement of Tertiary Propargylic Alcohols

Enzymatic spiroketal formation via oxidative rearrangement of pentangular polyketides

Enzymatic spiroketal formation via oxidative rearrangement of pentangular polyketides

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Four‐Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene **

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction

Oxidative rearrangement of (+)-sesamin by CYP92B14 co-generates twin dietary lignans in sesame

Oxidative rearrangement of (+)-sesamin by CYP92B14 co-generates twin dietary lignans in sesame

A single diiron enzyme catalyses the oxidative rearrangement of tryptophan to indole nitrile

A single diiron enzyme catalyses the oxidative rearrangement of tryptophan to indole nitrile

Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

Development of new chemical oxidative, step and atom efficient C-N and N-N bond forming coupling reactions

Development of new chemical oxidative, step and atom efficient C-N and N-N bond forming coupling reactions

Genome rearrangement algorithms

Hochschulschrift

Genome rearrangement algorithms

Cultural heritage institutions wishing to register will find more information here.

Fields marked * need to be filled in.

Username*

Please enter your username

Email*

Please enter your email address

Please do not fill this field

First name

Last name

Password*

Please enter your password

Confirm password*

Please enter the same password

I have read the terms of use and the privacy policy for the collection of personal data and accept them. *

This field is required.

I would like to subscribe to the newsletter of the Deutsche Digitale Bibliothek. See newsletter subscription info.

Account created

Your "My DDB" account has been successfully created. Before you can log in to your account, you must click the confirmation link in the message we just sent to the email address you provided.