A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

• Naoki Takeda,
• Shuichi Akasaka,
• Susumu Kawauchi and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2024, 20, 2234–2241, doi:10.3762/bjoc.20.191

• the strain-promoted double azide addition feature, DBA 5 was evaluated as a crosslinker for azidated polymers. After 5 (5 mol %) was added to a partially azidated poly(vinyl chloride) (PVC-N3) (x = 0.11, n = 1000) in THF, the solvent was gradually evaporated on a Teflon boat. The resulting self

• metal-free click reaction was employed to crosslink a partially azidated poly(vinyl chloride). The crosslinking proceeded by simply mixing the polymer and crosslinker in THF and evaporating, and the formation of the crosslinked polymer film was confirmed by the strain–stress curves. The developed method

• partially azidated poly(vinyl chloride) (PVA-N3) was prepared by stirring poly(vinyl chloride) and NaN3 in DMF at room temperature overnight. Measurements NMR spectra were recorded using a JEOL mode Al300 (300 MHz) at room temperature. Deuterated chloroform was used as the solvent unless otherwise stated

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

• Alexander V. Tsygankov,
• Vladyslav O. Vereshchak,
• Tetiana O. Savluk,
• Serhiy M. Desenko,
• Valeriia V. Ananieva,
• Oleksandr V. Buravov,
• Yana I. Sakhno,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

• of acid also led to the formation of amides 10b–d as main products and the corresponding ketobisamides 12d–e as minor products (Table 2, entries 10, 11, 18, 23, and 24). This can be explained by the formation of HCl in the reaction mixture due to the substitution of chlorine in the vinyl chloride

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• poly(vinyl chloride) (PVC) [14]. About half of the industrial polymers manufactured worldwide are produced by radical polymerization [15][16]. 1.2.1 Key features of radical polymerization: Radical polymerization, which has a classical chain reaction process, usually analyzed kinetically on the

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• view. Some recent examples are cited herein. Postconsumer PET was depolymerised in the melt (at 250 °C) using DEG and Ca/Zn stearate as catalyst, and the product mixture was used in situ in conjunction with bis(2-ethylhexyl)phthalate and the same metal promoter for the production of flexible poly(vinyl

• chloride) compounds [243]. One-pot depolymerisation–polycondensation reactions were developed to produce random copolyesters poly(ethylene terephthalate-co-adipate) from PET in the presence of EG and adipic acid [244]. The depolymerisation step was carried out using a zinc acetate catalyst (1 wt %), with

Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride

• Beatrice Lansbergen,
• Catherine S. Meister and
• Michael C. McLeod

Beilstein J. Org. Chem. 2021, 17, 404–409, doi:10.3762/bjoc.17.36

• rise to [6,7]bicyclic ketones 9, and 10 and the linear acid chloride 13, respectively. We have also found that when the ketone is not present, the trifluoroalkyl substrate is converted into bicyclic vinyl chloride 17 when treated with AlCl3. We hope that this short communication will inspire other

Design, synthesis and application of carbazole macrocycles in anion sensors

• Alo Rüütel,
• Ville Yrjänä,
• Sandip A. Kadam,
• Indrek Saar,
• Mihkel Ilisson,
• Astrid Darnell,
• Kristjan Haav,
• Tõiv Haljasorg,
• Lauri Toom,
• Johan Bobacka and
• Ivo Leito

Beilstein J. Org. Chem. 2020, 16, 1901–1914, doi:10.3762/bjoc.16.157

• and the ability to target a larger variety of ions compared to e.g. glass. Plasticizers may be required to improve transmembrane diffusion rates unless the polymer is self-plasticizing. Plasticized poly(vinyl chloride) (PVC), which was used in this study, is an example of a commonly used membrane

• from poly(vinyl chloride) plasticized with bis(2-ethylhexyl)sebacate (DOS), which was chosen since it was considered to be suitable for use in membranes with monovalent primary ions [5]. The compositions of the ISMs were 2 wt % ionophore, 50 mol % anion exchanger relative to the ionophore, 65 wt % DOS

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes

• Zhensheng Zhao and
• Graham K. Murphy

Beilstein J. Org. Chem. 2018, 14, 796–802, doi:10.3762/bjoc.14.67

• . Experimental evidence suggests that a radical mechanism is involved. Keywords: allene; chlorination; hypervalent iodine; synthetic methods; vinyl chloride; Introduction Organochlorine compounds are vital as polymer precursors [1], as pharmaceuticals [2][3] and agrochemicals [4][5][6] and as functional

The synthesis of functionalized bridged polycycles via C–H bond insertion

• Jiun-Le Shih,
• Po-An Chen and
• Jeremy A. May

Beilstein J. Org. Chem. 2016, 12, 985–999, doi:10.3762/bjoc.12.97

• insertion (Scheme 3) [26]. Here, an existing bridged ring with a pendant vinyl chloride was synthesized (see 15). The addition of base promoted the formation of a vinylidene carbene 16, which then inserted into the more electron-rich methine C–H bond to generate the fused cyclopentenyl ring in 17. While

Preparation of phosphines through C–P bond formation

• Iris Wauters,
• Wouter Debrouwer and
• Christian V. Stevens

Beilstein J. Org. Chem. 2014, 10, 1064–1096, doi:10.3762/bjoc.10.106

• easily be derived from the corresponding ketone and they are more reactive then the vinyl chloride or bromide during the oxidative addition. More recently also vinyl tosylates and enol phosphates have proven to be suitable reagents. The catalytic arylic C–P cross-coupling reaction can be a greener

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

• Sebastian Krüger and
• Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

• vinyl chloride using Vielsmeier’s reagent [163][164]. Dechlorination [165][166] was then achieved and yielded α,β-unsaturated aldehyde 195 upon hydrolysis. Grignard addition to the newly formed aldehyde followed by reoxidation furnished the side chain of compound 196. Treatment of unsaturated ketone 196

Anionic cascade reactions. One-pot assembly of (Z)-chloro-exo-methylenetetrahydrofurans from β-hydroxyketones

• István E. Markó and
• Florian T. Schevenels

Beilstein J. Org. Chem. 2013, 9, 1319–1325, doi:10.3762/bjoc.9.148

• -methylenetetrahydrofurans, a brief survey of their reactivity was performed. Several reactions involving the vinyl chloride function proved unsuccessful [28][29]. Attempts to perform oxidative rearrangement and dehydration failed and functionalisation of the hydroxy group appeared difficult [30][31]. Initially, the adduct

Natural product biosyntheses in cyanobacteria: A treasure trove of unique enzymes

• Jan-Christoph Kehr,
• Douglas Gatte Picchi and
• Elke Dittmann

Beilstein J. Org. Chem. 2011, 7, 1622–1635, doi:10.3762/bjoc.7.191

• ) Formation of the trichloroleucyl starter unit of barbamide (7) synthesis through the non-heme iron(II)-dependent halogenases BarB1 and BarB2. B) Formation of cyclopropane and vinyl chloride functional groups in curacin A (9) and jamaicamide A (8) biosynthesis, respectively. The halogenated carbon is