From the journal:

Chemical Communications

Quantifying the enamine-type nucleophilic reactivity of α-aryl vinyl azides

Prabaharan Thiruvengetam, ORCID logo a   Jan Brossette, ORCID logo a   Christoph Gross, ORCID logo a   Hendrik Zipse ORCID logo *a  and  Armin R. Ofial ORCID logo *a  

* Corresponding authors

a Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany
E-mail: zipse@cup.uni-muenchen.de, ofial@lmu.de

Abstract

Analyzing the kinetics of the reactions of α-aryl-substituted vinyl azides (VA) with benzhydrylium ions by using the relationship lg k2(20 °C) = sN(N + E) quantified the nucleophilic reactivity of VA in dichloromethane and Cyrene™. The nucleophilicities N of VA and of further styrenes correlate linearly with DFT-calculated methyl cation affinities, which facilitates the design of styrenes with predictable reactivity.

Graphical abstract: Quantifying the enamine-type nucleophilic reactivity of α-aryl vinyl azides

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Article information

DOI
https://doi.org/10.1039/D6CC00190D
Article type
Communication
Submitted
12 Jan 2026
Accepted
02 Feb 2026
First published
16 Feb 2026
This article is Open Access
Creative Commons BY license

Chem. Commun., 2026, Advance Article

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Quantifying the enamine-type nucleophilic reactivity of α-aryl vinyl azides

P. Thiruvengetam, J. Brossette, C. Gross, H. Zipse and A. R. Ofial, Chem. Commun., 2026, Advance Article , DOI: 10.1039/D6CC00190D

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