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Search for "chemical education" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Advancements in hydrochlorination of alkenes

Daniel S. Müller

Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72

50 mmol scale [60]. Little racemization (<7%) of 77 occurred during the reaction. The simplicity of the Kropp protocol resulted in a report in the journal of chemical education [61]. Similar work was reported by Delaude and co-workers [62]. They studied a series of zeolites for the hydrochlorination

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Graphical Abstract

Scheme 1: Classes of hydrochlorination reactions discussed in this review.

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Figure 1: Mayr’s nucleophilicity parameters for several alkenes. References for each compound can be consulte...

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Figure 2: Hydride affinities relating to the reactivity of the corresponding alkene towards hydrochlorination....

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Scheme 2: Distinction of polar hydrochlorination reactions.

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Scheme 3: Reactions of styrenes with HCl gas or HCl solutions.

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Figure 3: Normal temperature dependence for the hydrochlorination of (Z)-but-2-ene.

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Figure 4: Pentane slows down the hydrochlorination of 11.

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Scheme 4: Recently reported hydrochlorinations of styrenes with HCl gas or HCl solutions.

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Scheme 5: Hydrochlorination reactions with di- and trisubstituted alkenes.

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Scheme 6: Hydrochlorination of fatty acids with liquified HCl.

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Scheme 7: Hydrochlorination with HCl/DMPU solutions.

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Scheme 8: Hydrochlorination with HCl generated from EtOH and AcCl.

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Scheme 9: Hydrochlorination with HCl generated from H₂O and TMSCl.

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Scheme 10: Regioisomeric mixtures of chlorooctanes as a result of hydride shifts.

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Scheme 11: Regioisomeric mixtures of products as a result of methyl shifts.

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Scheme 12: Applications of the Kropp procedure on a preparative scale.

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Scheme 13: Curious example of polar anti-Markovnikov hydrochlorination.

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Scheme 14: Unexpected and expected hydrochlorinations with AlCl₃.

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Figure 5: Ex situ-generated HCl gas and in situ application for the hydrochlorination of activated alkenes (*...

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Scheme 15: HCl generated by Grob fragmentation of 92.

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Scheme 16: Formation of chlorophosphonium complex 104 and the reaction thereof with H₂O.

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Scheme 17: Snyder’s hydrochlorination with stoichiometric amounts of complex 104 or 108.

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Scheme 18: In situ generation of HCl by mixing of MsOH with CaCl₂.

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Scheme 19: First hydrochlorination of alkenes using hydrochloric acid.

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Scheme 20: Visible-light-promoted hydrochlorination.

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Scheme 21: Silica gel-promoted hydrochlorination of alkenes with hydrochloric acid.

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Scheme 22: Hydrochlorination with hydrochloric acid promoted by acetic acid or iron trichloride.

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Figure 6: Metal hydride hydrogen atom transfer reactions vs cationic reactions; BDE (bond-dissociation energy...

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Scheme 23: Carreira’s first report on radical hydrochlorinations of alkenes.

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Figure 7: Mechanism for the cobalt hydride hydrogen atom transfer reaction reported by Carreira.

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Scheme 24: Radical “hydrogenation” of alkenes; competing chlorination reactions.

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Scheme 25: Bogers iron-catalyzed radical hydrochlorination.

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Scheme 26: Hydrochlorination instead of hydrogenation product.

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Scheme 27: Optimization of the Boger protocol by researchers from Merck [88,89].

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Figure 8: Proposed mechanism for anti-Markovnikov hydrochlorination by Nicewicz.

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Scheme 28: anti-Markovnikov hydrochlorinations as reported by Nicewicz.

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Figure 9: Mechanism for anti-Markovnikov hydrochlorination according to Ritter.

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Scheme 29: anti-Markovnikov hydrochlorinations as reported by Nicewicz; rr (regioisomeric ratio) corresponds t...

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Scheme 30: anti-Markovnikov hydrochlorinations as reported by Liu.

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Review

Published 15 Apr 2024

Full text

NMRium: Teaching nuclear magnetic resonance spectra interpretation in an online platform

Luc Patiny,
Hamed Musallam,
Alejandro Bolaños,
Michaël Zasso,
Julien Wist,
Metin Karayilan,
Eva Ziegler,
Johannes C. Liermann and
Nils E. Schlörer

Beilstein J. Org. Chem. 2024, 20, 25–31, doi:10.3762/bjoc.20.4

data for publication, it also excels in enhancing teaching of NMR interpretation. In this paper, we present some current possibilities of this new tool. Several series of exercises are already provided on https://www.nmrium.org/teaching. Keywords: chemical education; E-learning; NMR; NMR spectra

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