Phenylseleno trifluoromethoxylation of alkenes

• Clément Delobel,
• Armen Panossian,
• Gilles Hanquet,
• Frédéric R. Leroux,
• Fabien Toulgoat and
• Thierry Billard

Beilstein J. Org. Chem. 2024, 20, 2434–2441, doi:10.3762/bjoc.20.207

• , entry 7). Finally, the reaction time was reduced from 24 h to 2.5 h without affecting the yield (Table 1, entry 8). In order to better understand the mechanism of the reaction, an NMR study of the premixing of DDPyOCF3 with PhSeBr was performed. The disappearance of the broad signal of CF3O− and the

• of the oxidative conditions used (mCPBA [75], H2O2 [75], selectfluor®/H2O [76], SO2Cl2/NaHCO3 (aq) [77][78]), in most cases a complex mixture was observed and no corresponding vinylic compound was detected by NMR. The phenylselenyl moiety could also undergo radical reduction to produce

• stirred at room temperature for 2.5 h (unless otherwise stated). Note that a yellowish precipitate is formed during the reaction for high yielding substrates. The reaction is monitored by 19F NMR (PhCF3 as internal standard). At the end of the reaction, the content of the vial is transferred to a

Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles

• Yutaro Miyashita,
• Sae Someya,
• Tomoko Kawasaki-Takasuka,
• Tomohiro Agou and
• Takashi Yamazaki

Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206

• during the lactone-forming process. Their close structural resemblance led to a significant peak overlap both in the 1H and 19F NMR spectra which made it difficult to obtain their exact ratio and thus, the combined 19F NMR yields were shown in Table 4. Separation of these two compounds was eventually

• the complex mixture after mixing 2b with t-BuOK and nitroacetate in DMSO at 80 °C, the unexpected compound 2,3-dihydroxybutyrate anti-10a was isolated as a single isomer. Its production was also detected by 19F NMR from the reaction mixture when nitromethane (16%) and ethyl (diethylphosphono)acetate

• of the reductive elimination very slow, the intermediary Cu(III) species safely existed until the addition of D2O. Because the significant overlap of NMR peaks was observed due to the quite similar structure of 11a and 11a-D, quantitative analysis of the deuterium content of 11a-D was not possible

Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt

• Dominik L. Reinhard,
• Anna Schmidt,
• Marc Sons,
• Julian Wolf,
• Elric Engelage and
• Stefan M. Huber

Beilstein J. Org. Chem. 2024, 20, 2401–2407, doi:10.3762/bjoc.20.204

• )AuCl was applied with a catalyst loading of 2 mol %, activated by an equal amount of the DAI salt. Due to solubility issues, the reaction had to be performed in methylene chloride instead of chloroform. The gold-catalyzed cyclization reaction (Scheme 2) was followed via 1H NMR spectroscopy (Figure 3

• , several control experiments were also performed, even though the benchmark reaction has already been established in halogen-bonding activation. In the presence of 2 mol % of either the unactivated gold complex (PPh3)AuCl or the XB donors 1BArF–4BArF + 7BArF, 1H NMR showed no conversion within 18 h

• , indicating that the activated gold complex is the catalytically active species. Furthermore, stability measurements (1H and 19F NMR) of 1:1 mixtures of the gold complex and the XB donors were performed in order to investigate the stability of the cationic iodonium structures towards the gold complex [28

Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO

• Hisanori Senboku and
• Mizuki Hayama

Beilstein J. Org. Chem. 2024, 20, 2392–2400, doi:10.3762/bjoc.20.203

• in less than 10% yield, determined through 1H NMR analysis, except for Table 1, entries 3 (13%) and 5 (25%). It should also be noted that electrolysis was carried out at room temperature, but the temperature of the reaction mixture increased to 40–50 °C at the end of the electrolysis in every case

• of dechlorinated diphenylmethanol (1a) in the recovered starting material were confirmed by 1H NMR analysis. These results suggested that 2a was produced from 1a, which was generated in situ by electroreductive dechlorination of 1b. In other words, electroreductive dechlorination of 1b, producing 1a

• , took place preferentially over electroreductive C(sp3)–O bond cleavage of 1b. It should also be noted that no aromatic carboxylic acids were detected by 1H NMR analysis. In contrast, the electrochemical carboxylation of 1c, containing a fluorine atom, gave a mixture of fluorine-containing carboxylic

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• , compounds 6–9 are products of alkylation of the nitrogen atom of the heterocycle. Thiones 6–9 were obtained in 40–79% yield (Scheme 1,b). The structures of synthesized compounds were confirmed by the spectral methods IR-, 1H NMR, 13C{1H} NMR spectroscopy (Figures S1–S18 in Supporting Information File 1

• oxidation peak of the catechol fragment to the cathode region (Figure 7). This is due to the less acceptor nature of the thiazole ring compared to the more electron-deficient oxadiazole cycle, which contains three heteroatoms. In addition, according to NMR spectral data, one proton of the hydroxy group of

Asymmetric organocatalytic synthesis of chiral homoallylic amines

• Nikolay S. Kondratyev and
• Andrei V. Malkov

Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201

• two enantiotopic faces of acylimine 2, exposing only one face to the attack by the allyl group. The replacement of one isopropoxy (iPrO) group between allylboronate 1 with BINOL was confirmed by ESI-MS and NMR analysis of the reaction mixture. Interestingly, both (E)- and (Z)-crotyl boronates 6 and 8

• active catalytic species in COBI-catalysed allylations, chemical equilibria in a solution containing catalyst 72, triflic acid, and aldimine 73 were investigated by low-temperature NMR spectroscopy (Scheme 15). Protonation of oxazaborolidine 70 with triflic acid resulted in an 8.3:1 mixture of 71 and 72

• , in the COBI–imine complex 74 it appears at 8.41 ppm, while in the imine TfOH salt 75 it shows at 9.24 ppm. This detailed NMR investigation sparked further interest in the structure of the transition state of this reaction. An analysis of the potential energy profiles of the two hypothetical pathways

Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system

• Yuri A. Sidunets,
• Valeriya G. Melekhina and
• Leonid L. Fershtat

Beilstein J. Org. Chem. 2024, 20, 2342–2348, doi:10.3762/bjoc.20.200

• , indicating that the developed tandem protocol does not depend on the presence of the N-oxide moiety in the parent heterocycle. All synthesized triazinones 1 and 7 were fully characterized by IR, 1H and 13C NMR spectroscopy, and high-resolution mass spectrometry. The structure of compounds 1b and 7h was

• obtained. Thus, we have demonstrated that the terminal nitrogen atom in the diazonium fragment of intermediate 9 becomes the N5 atom of compound 8 (corresponding 15N NMR spectra are provided in Supporting Information File 1). To explore the potential application of the obtained compounds 1 and 7, we

• . Supporting Information Supporting Information File 96: Experimental procedures, characterization data of all products, copies of 1H, 13C NMR, 15N spectra of new compounds, DSC curves,X-ray crystallographic data and copies of IR spectra. Acknowledgements The crystal structure determination was performed at

Stereoselective mechanochemical synthesis of thiomalonate Michael adducts via iminium catalysis by chiral primary amines

• Michał Błauciak,
• Dominika Andrzejczyk,
• Błażej Dziuk and
• Rafał Kowalczyk

Beilstein J. Org. Chem. 2024, 20, 2313–2322, doi:10.3762/bjoc.20.198

• cyclohexenone. Addition of bisthiomalonates 1–3 to cyclopentenone. Acyclic enone in reactions with thiomalonates 1–4. Reaction of β-ketothioesters with acceptor E1. Supporting Information Supporting Information File 94: Experimental and analytical data, crystallographic information and NMR spectra

Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes

• Phong Thai,
• Lauv Patel,
• Diyasha Manna and
• David C. Powers

Beilstein J. Org. Chem. 2024, 20, 2305–2312, doi:10.3762/bjoc.20.197

• iminoiodinanes for the metal-free aziridination of unactivated olefins. 1H NMR and cyclic voltammetry (CV) studies indicate that hydrogen-bonding between HFIP and the iminoiodinane generates an oxidant capable of direct NGT to unactivated olefins. Stereochemical scrambling during aziridination of 1,2

• catalysis (Table 1, entry 1) [40][41]. In contrast, combination of PhINTs (2.0 equiv) with 1a in HFIP afforded 3a in 67% NMR yield (Table 1, entry 2). Lowering the loading of iminoiodinane 2a to 1.5 or 1.0 equivalents decreased the reaction yield to 28% and 22%, respectively (Table 1, entries 3 and 4

• unprotected alcohol is tolerated in our procedure, with product 3l delivered at 50% NMR yield; 3l is sensitive to column chromatography, and thus aziridine-opening to a cyclic ether was observed (31% isolated yield) during purification. Aziridination of cis- or trans-4-octene afforded aziridine 3m as a 1.3

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

• Stefan P. Schmid,
• Leon Schlosser,
• Frank Glorius and
• Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

• properties via descriptors. Apart from molecular vibrations, electronic influences are commonly modelled via global properties of a molecule (such as HOMO/LUMO energies) or local properties (such as natural population analysis (NPA) charges/NMR shifts), as shown in Figure 5 [69][72][88][89]. With respect to

Deuterated reagents in multicomponent reactions to afford deuterium-labeled products

• Kevin Schofield,
• Shayna Maddern,
• Yueteng Zhang,
• Grace E. Mastin,
• Rachel Knight,
• Wei Wang,
• James Galligan and
• Christopher Hulme

Beilstein J. Org. Chem. 2024, 20, 2270–2279, doi:10.3762/bjoc.20.195

• . Optimization of deuterated Leuckart–Wallach reactiona. Microsomal stability package of deuterated and non-deuterated dihydropyridines. Supporting Information Supporting Information File 86: Experimental and analytical data and copies of NMR spectra. Acknowledgements We thank the UA mass spectrometry and NMR

gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu₄NBF₄ or electrogenerated acid

• Mizuki Yamaguchi,
• Hiroki Shimao,
• Kengo Hamasaki,
• Keiji Nishiwaki,
• Shigenori Kashimura and
• Kouichi Matsumoto

Beilstein J. Org. Chem. 2024, 20, 2261–2269, doi:10.3762/bjoc.20.194

• (NMR) yield, in which trifluorotoluene (CF3C6H5) was used as an internal standard. The use of Tf2NH (5 equiv or 10 equiv) and Bu4NBF4 (5 equiv) in CH2Cl2 at room temperature gave the corresponding product 2a in up to 83% yield (Table 1, entries 1–5). The use of CF3COOH did not yield 2a at all (Table 1

• in the presence of the substrate. The total electricity of 3.0 F/mol vs 1a was passed to the solution. Interestingly, the result gave the corresponding difluorinated compound 2a in 29% yield in the case of 8 mA, as shown by 19F NMR analysis. In addition, 2a was obtained in 42% yield by 19F NMR

• oxidation of method B was conducted by using 8 mA. The reaction of but-3-yn-1-ylbenzene (1b) in method A gave the corresponding compound 2b in 21% isolated yield (Table 2, entry 1). The 19F NMR result indicated 63% yield. Because of the low molecular weight of 2b, the isolated yield might be somewhat lower

Synthesis and reactivity of the di(9-anthryl)methyl radical

• Tomohiko Nishiuchi,
• Kazuma Takahashi,
• Yuta Makihara and
• Takashi Kubo

Beilstein J. Org. Chem. 2024, 20, 2254–2260, doi:10.3762/bjoc.20.193

• , indicating that the high reactivity of the central sp2 carbon. To evaluate the decomposition pathway, the decomposed materials were characterized. Surprisingly, the major compound detected by 1H NMR measurement of the crude material was compound 1, along with di(10-mesityl-9-anthryl)methane (4) as a minor

• O–O bond cleavage to give compounds 1 and 5 (Scheme 2). Owing to the high reactivity of the DAntM radical, cyclic voltammogram (CV) was measured by using the stable DAntM cation, prepared from compound 3 oxidized by antimony(V) chloride, which can be characterized by 1H, 13C NMR, and UV–vis

• . Decomposition pathway of the DAntM radical under air conditions. Supporting Information Supporting Information File 81: Synthetic procedure and compound characterization data (1H, 13C NMR, MS, melting point, X-ray crystallography) of new compounds. DFT calculation results and optimized structural Cartesian

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

• indicates that the formed double azide adduct is 6a, which is consistent with our previous report [18]. The double azide addition was further investigated by changing the reaction temperature. The rate constant was determined by the temperature-dependent 1H NMR spectra in CDCl3. The reaction kinetics

• previously reported electron-donating hexyloxy substituents. The addition pattern was experimentally investigated by 2D NMR, which was also supported by DFT calculations. The bistriazole product displayed fluorescence in the visible range with a fluorescence quantum yield of 7.0%. Finally, the developed

• 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

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

• Haifeng Yu,
• Wanting Zhang,
• Xuejing Cui,
• Zida Liu,
• Xifu Zhang and
• Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

• by other acids such as H2SO4 and CF3SO3H, the reaction showed poor effectiveness due to the poor solubility of 1a in water (Table 1, entries 4 and 5). Most notably, 2a was an inseparable mixture of keto and enol isomers, reaching a keto/enol ratio of 5:4 as determined by 1H NMR spectroscopy. Thus

• thioesters and β-keto amides by simply changing reaction conditions. These features, including a good substrate scope, excellent yield and selectivity and ease of scale-up, rendered the green hydrolysis reaction very environment-friendly, practical, and attractive. Experimental 1H and 13C{1H} NMR spectra

• . Reaction conditions A: 1 (0.25 mmol), DBSA (87.9 mg, 0.25 mmol), H2O (1 mL), reflux, 5 h. Isolated yield is stated. Keto/enol ratio of 2 was determined by 1H NMR spectroscopy. Synthesis of β-keto amides 3. Reaction conditions B: 1 (0.25 mmol), NaOH (0.75 mmol, 30 mg), H2O (1 mL), reflux, 24 h. Isolated

Electrochemical allylations in a deep eutectic solvent

• Sophia Taylor and
• Scott T. Handy

Beilstein J. Org. Chem. 2024, 20, 2217–2224, doi:10.3762/bjoc.20.189

• partial solubility of ethylene glycol in methoxycyclopentane as ethylene glycol could be clearly seen in the 1H NMR spectrum of the crude reaction extracts. It should also be noted that the lower isolated yields most likely reflect mechanical losses during extraction and chromatographic separation as the

• funnel with the aid of 10 mL of deionized (DI) water followed by 20 mL of diethyl ether. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered, and the solvent removed in vacuo to afford the crude product, which was first analyzed by 1H NMR spectroscopy and then purified using

• sulfate, filtered, and the solvent removed in vacuo to afford the crude product, which was first analyzed by 1H NMR spectroscopy and then purified using flash column chromatography. The graphite electrodes were not polished in between reactions, but were rinsed with DI water and then acetone. General Sn

Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

• Andrey R. Galeev,
• Maksim V. Dmitriev,
• Alexander S. Novikov and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2024, 20, 2208–2216, doi:10.3762/bjoc.20.188

• reaction was expected, Figure 2) with morpholine under previously found conditions (Scheme 2). To our delight, the meta-1,2,4-oxadiazole aniline 3ab, formed by the sequence of aldol-type reactions, was isolated in 80% yield and its structure was confirmed by NMR and single crystal X-ray analysis (CCDC

• data of new compounds and NMR spectra. Supporting Information File 64: xyz files with Cartesian atomic coordinates for all model structures and CIF-files for compounds 1g, 3ab, 3bb and 3ca. Funding This study was performed under financial support of the Ministry of Science and Higher Education of the

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

• : Total synthesis and comparison of the NMR spectra revealed that this natural product is identical with altertenuol [41], whose structure was correctly given previously [42]. Furthermore, the originally proposed structures [43] of graphislactones E and F were corrected after total synthesis and

• comparison of NMR spectra [44]. Occasionally, natural products have been reported more than one time as new compounds and were given several names. Only the first given name should be used and further names are thus obsolete: Verrulactone D is erroneously given in the SciFinder database as synonym for

• from an unidentified endophytic fungus [124] and later from colletotrichum sp. [125], Lachnum abnorme [126], Diaporthe phragmitis [127] and a further D. sp. [128], and deviantly from the flower buds of the banana species Musa nana [129]. Its structure was determined by NMR spectroscopy [126] and

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• purified through silica-gel column chromatography. After successfully synthesizing these easy-to-make yet interesting molecules, they were fully characterized by means of the standard spectroscopic techniques (1H NMR, 13C NMR and HRMS). We are of the opinion that these truxene-based systems will be useful

• derivatives were successfully characterized and their structures were established by means of the 1H and 13C NMR spectroscopy, besides further confirmation by mass spectrometry (see Supporting Information File 1). The UV–vis absorption, emission and time-resolved fluorescence spectra Emission and absorption

• like 1H NMR, 13C NMR, and mass spectral data. The preliminary UV–vis absorption as well as fluorescence emission spectral data for thus prepared truxene-based compounds were recorded in chloroform and compared as well. Additionally, time-resolved fluorescence lifetime decays were also measured for thus

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• in our study (Table 1, entries 1–6), but in any case, we received a mixture of regioisomeric products 2a/2a’ (3:1 to 2:1) confirmed by 2D NMR spectroscopy (see Supporting Information File 1, Figures S1–S6). Classical conditions for Biginelli reaction (reflux in ethanolic HCl) gave only 23% yield

• ]. We hope that compound 2r and its analogues obtained in this work can be further deeply studied by in silico and in vitro methods to discover the compound most suitable for clinical trials. The structures of the synthesized compounds 2a–r were confirmed by spectral data. The 1H NMR spectra of the

• signals clearly corresponds to the heterocycles depicted above. Figure S8 (see Supporting Information File 1) shows 1H NMR spectra for Ph-substituted O,S,Se-DHPMs 2a,h,o. It can be seen from them that when going from oxygen to selenium (2h→2a→2o), the signals of both NH groups shift to down field (7.87

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

• Akiya Ogawa and
• Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

• . Because of this conjugation, the aromatic ring at the N of the 1,1-addition product 4 (R = Ar, E = PhS) geometrically isomerizes faster than the NMR timescale, so that the two thio groups of 4 are observed to be equivalent in NMR spectroscopy. In the case of diphenyl diselenide as a representative organic

From perfluoroalkyl aryl sulfoxides to ortho thioethers

• Yang Li,
• Guillaume Dagousset,
• Emmanuel Magnier and
• Bruce Pégot

Beilstein J. Org. Chem. 2024, 20, 2108–2113, doi:10.3762/bjoc.20.181

• decided to use 2 equivalents of DIPEA at low temperature. After ten minutes at −15 °C to allow for the reaction between phenyl trifluoromethyl sulfoxide (1a) and acetonitrile, the base was added and the reaction was stirred for the same amount of time. To our delight, a good NMR yield of 74% was received

• 1h–j proved also efficient for this rearrangement giving rise to the corresponding thioethers 2h–j in good NMR yields and lower isolated yield in the case of the more volatile adduct 2i. Finally, trifluoromethyl selenoxide 1k was tested as a substrate, and the rearranged product was obtained in a low

• equiv) was slowly added to the flask with a syringe and the reaction was stirred for another 10 min. At the end of the reaction, 1 mL of chloroform and a known amount of trifluoromethoxybenzene were added to the flask in order to determine the 19F NMR yield. To purify the product, the reaction mixture

Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

• needed to deeply investigate the multifaceted aspects of protein–glycan interactions. To date, advanced and versatile NMR, X-ray crystallography, and MS methods [36][37][38] above all, have been developed to reach extensive information on the structural and conformational features of glycans and proteins

• publicly accessible platform for multiple glycoinformatic studies and web tools, which among the other services allows the users to locate adiabatic maps for specific glycosidic linkages. Generally, CSDB offers a wealth of valuable features; it provides structural, bibliographic, taxonomic, NMR

• , keywords, biological source data up to strains, methods used to elucidate structures, NMR signal assignment and other information (http://csdb.glycoscience.ru/database/). 2. Disac3DB: free annotated database that contains the 3D structural information of about 120 entries of disaccharides. For each

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates

• Deepa Nair,
• Abhishek Tiwari,
• Banamali Laha and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2024, 20, 2016–2023, doi:10.3762/bjoc.20.177

• undergoing yet another diastereoselective 6-endo-trig intramolecular oxa-Michael addition. The structure and stereochemistry of compounds 3 and 4 were confirmed by 1H-1H-COSY and 1H-1H-NOESY NMR experiments. This was further unambiguously established by single crystal X-ray analysis of a representative

• . Reaction optimisation using phase-transfer catalysts.a Scope of alkylidenemalonates and curcumins.a Supporting Information Supporting Information File 38: Experimental procedures and characterization data. Supporting Information File 39: Copies of NMR spectra of all new compounds. Supporting Information

Understanding X-ray-induced isomerisation in photoswitchable surfactant assemblies

• Beatrice E. Jones,
• Camille Blayo,
• Jake L. Greenfield,
• Matthew J. Fuchter,
• Nathan Cowieson and
• Rachel C. Evans

Beilstein J. Org. Chem. 2024, 20, 2005–2015, doi:10.3762/bjoc.20.176

• the samples ex-situ for 3.5 hours to achieve a Z-rich PSS, where the percentage isomerised has been determined previously using 1H NMR spectroscopy [20]. The 10 wt % sample was measured over 800 X-ray exposures of 250 ms each. The initial Z-rich PSS SAXS pattern shows a strong interaction peak at Q

• ± 4% E-to-Z isomerisation for 10 and 90 wt % AAPTAB, respectively, as determined previously using 1H NMR [20]. SAXS SAXS measurements were performed at the high-throughput SAXS beamline B21, Diamond Light Source (Oxfordshire, UK) [47]. The X-ray beam energy was 13.0 keV and the detector distance set