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Search for "McKenna’s reaction" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

The McKenna reaction – avoiding side reactions in phosphonate deprotection

Katarzyna Justyna,
Joanna Małolepsza,
Damian Kusy,
Waldemar Maniukiewicz and
Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 1436–1446, doi:10.3762/bjoc.16.119

compounds, which should remain intact under McKenna’s reaction conditions, we synthesized analogs 9, and 10–13 (Figure 1). Among the representative functional groups, we selected compounds comprising a triple (10) and a double (11) bond, both susceptible to HBr addition. Compounds 12 and 9a–d were selected

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Scheme 1: Schematic overview of the McKenna reaction including the decomposition of BTMS in protic solvents. ...

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Figure 1: The model compounds used for this study (in red: the functionality of the molecules vulnerable to s...

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Scheme 2: Formation of the side products derived from 10. Conditions: An equimolar mixture of propargylamide ...

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Scheme 3: Addition of HBr to compound 11.

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Scheme 4: N-Alkylation of 9.

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Scheme 5: N-Alkylation of 12.

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Scheme 6: Exchange of the chlorine substituent with bromine in 2-chloro-N-phenethylacetamide (13) under McKen...

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Full Research Paper

Published 23 Jun 2020

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Phosphonic acid: preparation and applications

Charlotte M. Sevrain,
Mathieu Berchel,
Hélène Couthon and
Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

the best methods to prepare phosphonic acids. Keywords: bromotrimethylsilane; hydrolysis; McKenna’s reaction; phosphonate; phosphonic acid; Review 1. Introduction Phosphonic acid is a functional group featuring two hydroxy moieties, one P=O double bond and one P–C bond. This functional group was

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Figure 1: Summary of the synthetic routes to prepare phosphonic acids detailed in this review. The numbers in...

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Figure 2: Chemical structure of dialkyl phosphonate, phosphonic acid and illustration of the simplest phospho...

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Figure 3: Illustration of some phosphonic acid exhibiting bioactive properties. A) Phosphonic acids for biome...

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Figure 4: Illustration of the use of phosphonic acids for their coordination properties and their ability to ...

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Figure 5: Hydrolysis of dialkyl phosphonate to phosphonic acid under acidic conditions.

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Figure 6: Examples of phosphonic acids prepared by hydrolysis of dialkylphosphonate with HCl 35% at reflux (16...

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Figure 7: A) and B) Observation of P–C bond breaking during the hydrolysis of phosphonate with concentrated H...

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Figure 8: Mechanism of the hydrolysis of dialkyl phosphonate with HCl in water.

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Figure 9: Hydrolysis of bis-tert-butyl phosphonate 28 into phosphonic acid 29 [137].

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Figure 10: A) Hydrolysis of diphenyl phosphonate into phosphonic acid in acidic media. B) Examples of phosphon...

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Figure 11: Suggested mechanism occurring for the first step of the hydrolysis of diphenyl phosphonate into pho...

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Figure 12: A) Hydrogenolysis of dibenzyl phosphonate to phosphonic acid. B) Compounds 33, 34 and 35 were prepa...

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Figure 13: A) Preparation of phosphonic acid from diphenyl phosphonate with the Adam’s catalyst. B) Compounds ...

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Figure 14: Suggested mechanism for the preparation of phosphonic acid from dialkyl phosphonate using bromotrim...

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Figure 15: A) Reaction of the phosphonate-thiophosphonate 37 with iodotrimethylsilane followed by methanolysis...

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Figure 16: Synthesis of hydroxymethylenebisphosphonic acid by reaction of tris(trimethylsilyl) phosphite with ...

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Figure 17: Synthesis of the phosphonic acid disodium salt 48 by reaction of mono-hydrolysed phosphonate 47 wit...

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Figure 18: Phosphonic acid synthesized by the sequence 1) bromotrimethylsilane 2) methanolysis or hydrolysis. ...

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Figure 19: Polyphosphonic acids and macromolecular compounds prepared by the hydrolysis of dialkyl phosphonate...

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Figure 20: Examples of organometallic complexes functionalized with phosphonic acids that were prepared by the...

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Figure 21: Side reaction observed during the hydrolysis of methacrylate monomer functionalized with phosphonic...

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Figure 22: Influence of the reaction time during the hydrolysis of compound 76.

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Figure 23: Dealkylation of dialkyl phosphonates with boron tribromide.

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Figure 24: Dealkylation of diethylphosphonate 81 with TMS-OTf.

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Figure 25: Synthesis of substituted phenylphosphonic acid 85 from the phenyldichlorophosphine 83.

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Figure 26: Hydrolysis of substituted phenyldichlorophosphine oxide 86 under basic conditions.

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Figure 27: A) Illustration of the synthesis of chiral phosphonic acids from phosphonodiamides. B) Examples of ...

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Figure 28: A) Illustration of the synthesis of the phosphonic acid 98 from phosphonodiamide 97. B) Use of cycl...

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Figure 29: Synthesis of tris(phosphonophenyl)phosphine 109.

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Figure 30: Moedritzer–Irani reaction starting from A) primary amine or B) secondary amine. C) Examples of phos...

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Figure 31: Phosphonic acid-functionalized polymers prepared by Moedritzer–Irani reaction.

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Figure 32: Reaction of phosphorous acid with imine in the absence of solvent.

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Figure 33: A) Reaction of phosphorous acid with nitrile and examples of aminomethylene bis-phosphonic acids. B...

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Figure 34: Reaction of carboxylic acid with phosphorous acid and examples of compounds prepared by this way.

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Figure 35: Synthesis of phosphonic acid by oxidation of phosphinic acid (also identified as phosphonous acid).

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Figure 36: Selection of reaction conditions to prepare phosphonic acids from phosphinic acids.

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Figure 37: Synthesis of phosphonic acid from carboxylic acid and white phosphorus.

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Figure 38: Synthesis of benzylphosphonic acid 136 from benzaldehyde and red phosphorus.

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Figure 39: Synthesis of graphene phosphonic acid 137 from graphite and red phosphorus.

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Published 20 Oct 2017

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