Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

• Celine Bittner,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2019, 15, 2534–2543, doi:10.3762/bjoc.15.246

• solutions of 1a and 1b after layering with pentane or hexane, respectively, crystals suitable for X-ray diffraction analysis could be obtained. The corresponding ORTEP drawings are given in Figure 3 and Figure 4. Ferrocene 1a crystallises in the orthorhombic space group Pca21, while the analogues compound

• disorder on the iron position. Unfortunately, no single crystals for X-ray diffraction analysis could be obtained with such disorder being absent. For the catalytic RCAM (Scheme 1), the substrates 1a and 1b were dissolved in toluene at high dilution (4.5 mM), and the catalyst MoF6 (2 mol %) was added as a

• experimental section in Supporting Information File 1). Crystals of 2a suitable for X-ray diffraction analysis could be obtained from a hot saturated solution in toluene after cooling to −28 °C. An ORTEP drawing is given in Figure 5. The ferrocenophane 2a crystallises in the orthorhombic space group Pbcn with

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

• Zhen Cao,
• Aline Lacoudre,
• Cybille Rossy and
• Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

• for 1a, AgOTFA for 1b, AgNO3 for 1c and PPh3AgOTf for 1d. Crystallographic structures of silver complexes Single crystals of 1a, 1c and 1d suitable for X-ray diffraction analysis were grown from the slow diffusion of hexane into a solution of each complex in dichloromethane. Interestingly, each

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

• -corona[6]arenes in the solid state, high quality single crystals of 3a were grown at room temperature from diffusion of diethyl ether vapor into the solution of 3a in acetonitrile. X-ray diffraction analysis revealed that the macrocycle 3a adopted an interesting conformation. As depicted in Figure 1, it

Synthesis of ([1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl)phosphonates and their benzo derivatives via 5-exo-dig cyclization

• Aleksandr S. Krylov,
• Artem A. Petrosian,
• Julia L. Piterskaya,
• Nataly I. Svintsitskaya and
• Albina V. Dogadina

Beilstein J. Org. Chem. 2019, 15, 1563–1568, doi:10.3762/bjoc.15.159

• of spin–spin interaction with the phosphorus nucleus at 23.43–28.99 ppm (1JСР = 143 Hz) and 53.5–72.1 ppm (2JCP = 7 Hz), respectively. In addition, the structure of phosphonate 14b was unambiguously proved by single crystal X-ray diffraction analysis. Probably, the reaction proceeds through the

Introduction of an isoxazoline unit to the β-position of porphyrin via regioselective 1,3-dipolar cycloaddition reaction

• Xiujun Liu,
• Xiang Ma and
• Yaqing Feng

Beilstein J. Org. Chem. 2019, 15, 1434–1440, doi:10.3762/bjoc.15.143

• linked to the porphyrin is still elusive. Later, a single crystal of 3a was obtained by diffusion of n-hexane to the solution of 3a in CHCl3 at 23 °C. The structure of 3a was unambiguously established by single-crystal X-ray diffraction analysis. Compound 3a crystallized in the monoclinic with space

Insertion of [1.1.1]propellane into aromatic disulfides

• Robin M. Bär,
• Gregor Heinrich,
• Martin Nieger,
• Olaf Fuhr and
• Stefan Bräse

Beilstein J. Org. Chem. 2019, 15, 1172–1180, doi:10.3762/bjoc.15.114

• in most cases. Single crystal X-ray diffraction analysis confirms the rod-like structure of the [2]staffanes that is often required in material applications. Keywords: bicyclo[1.1.1]pentane; bioisosteres; disulfides; linkers; [1.1.1]propellane; Introduction Rigid structures are emerging in both

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• the intense signals that occur due to cleavage of the CF3COO− anion. Single crystal X-ray diffraction analysis of biphenyl compound 9i has finally proved the structures of the obtained products (Figure 3). Compound 9i exists as organic salt with trifluoroacetic acid in the crystal phase. The existence

Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors

• Kirill B. Polyanskii,
• Kseniia A. Alekseeva,
• Pavel V. Raspertov,
• Pavel A. Kumandin,
• Eugeniya V. Nikitina,
• Atash V. Gurbanov and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2019, 15, 769–779, doi:10.3762/bjoc.15.73

• were obtained as good crystals suitable for X-ray diffraction analysis. Unfortunately, we were not able to obtain single crystals of satisfactory quality for the morpholino-containing catalyst 11d. Still, the accessible X-ray structural information is sufficient to correlate structure with catalytic

Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction

• Vaida Milišiūnaitė,
• Rūta Paulavičiūtė,
• Eglė Arbačiauskienė,
• Vytas Martynaitis,
• Wolfgang Holzer and
• Algirdas Šačkus

Beilstein J. Org. Chem. 2019, 15, 679–684, doi:10.3762/bjoc.15.62

• ) data and a single-crystal X-ray diffraction analysis. The 1H NMR spectra of compounds 4a–j revealed the characteristic H-3 proton singlet in the δ 7.60–7.77 ppm region as well as a H-4 proton singlet in the δ 6.06–6.74 ppm region. The 13C NMR spectra of 4a–j exhibited signals for the five carbon atoms

Reusable and highly enantioselective water-soluble Ru(II)-Amm-Pheox catalyst for intramolecular cyclopropanation of diazo compounds

• Hamada S. A. Mandour,
• Yoko Nakagawa,
• Masaya Tone,
• Hayato Inoue,
• Nansalmaa Otog,
• Ikuhide Fujisawa,
• Soda Chanthamath and
• Seiji Iwasa

Beilstein J. Org. Chem. 2019, 15, 357–363, doi:10.3762/bjoc.15.31

• determined to be (1S,5R,6R) by single-crystal X-ray diffraction analysis (Supporting Information File 1) [51]. Since the stereoselectivity of products depends on the cis/trans geometry of the reactants, other stereoisomers such as the (1S,5R,6S) product was not formed in this catalytic cyclopropanation

Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

• Hiroshi Morikawa,
• Jun-ichi Yamaguchi,
• Shun-ichi Sugimura,
• Masato Minamoto,
• Yuuta Gorou,
• Hisatoyo Morinaga and
• Suguru Motokucho

Beilstein J. Org. Chem. 2019, 15, 130–136, doi:10.3762/bjoc.15.13

• those of LM5CCs by reference to the a and c signals in Figure 4. The coupling constants for the signal a support the structures shown in Figure 5. Indeed, the equatorial position of the isopropenyl group for 2c and 2d in the solid state was confirmed by X-ray diffraction analysis, as reported previously

Synthesis, biophysical properties, and RNase H activity of 6’-difluoro[4.3.0]bicyclo-DNA

• Sibylle Frei,
• Adam K. Katolik and
• Christian J. Leumann

Beilstein J. Org. Chem. 2019, 15, 79–88, doi:10.3762/bjoc.15.9

• [43][44] followed by phosphitylation at the 3’-oxygen afforded the phosphoramidite 9. X-ray structure and molecular modeling of the 6’-diF-bc4,3 nucleoside To verify the relative configuration of nucleoside 6, crystals of this compound were subjected to X-ray diffraction analysis. The asymmetric unit

Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex

• Henrike Ehrhorn,
• Janin Schlösser,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2018, 14, 2425–2434, doi:10.3762/bjoc.14.220

• formation of the complex [W2{OC(CF3)Me2}6(NHMe2)] (W2F3·NHMe2) (Scheme 2). The additional amine ligand stems from the protonolysis reaction of the amide with the fluorinated alcohol. Brown crystals suitable for X-ray diffraction analysis were isolated from a saturated pentane solution at −40 °C. The

• molecular structure of this complex was established by X-ray diffraction analysis. The ORTEP diagram is shown in Figure 2, and selected bond lengths and angles are displayed in Table 1. The tungsten–tungsten triple bond of 2.3452(2) Å falls in the range of previously reported bond lengths of this type [69

• from [NaW2Cl7(THF)5] [86]. The 13C and 19F NMR spectra are also consistent with literature values. Crystals of W2F3 suitable for X-ray diffraction analysis were obtained upon cooling a saturated pentane solution to −40 °C. Unfortunately, the crystal structure suffers from severe disorder. Each tungsten

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

• Ana-Maria Preda,
• Małgorzata Krasowska,
• Lydia Wrobel,
• Philipp Kitschke,
• Phil C. Andrews,
• Jonathan G. MacLellan,
• Lutz Mertens,
• Marcus Korb,
• Tobias Rüffer,
• Heinrich Lang,
• Alexander A. Auer and
• Michael Mehring

Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

• rarely a more compact morphology. Both types of crystals of 2 were suitable for single crystal X-ray diffraction analysis and revealed the formation of two polymorphs 2a (colorless acicular crystals) and 2b (light yellow block-shaped crystals) in the solid state. Polymorph 2a crystallizes in the

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

• Siva Sankar Murthy Bandaru,
• Darinka Dzubiel,
• Heiko Ihmels,
• Mohebodin Karbasiyoun,
• Mohamed M. A. Mahmoud and
• Carola Schulzke

Beilstein J. Org. Chem. 2018, 14, 1871–1884, doi:10.3762/bjoc.14.161

• , so that the pure products were only available by crystallization from appropriate solvents, which resulted in lower yields of these products. Single crystal X-ray diffraction analysis of 9-(arylethynyl)benzo[b]quinolizinium derivatives 2a and 2b Single crystals of derivatives 2a and 2b were obtained

Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant

• Irina A. Mironova,
• Pavel S. Postnikov,
• Rosa Y. Yusubova,
• Akira Yoshimura,
• Thomas Wirth,
• Viktor V. Zhdankin,
• Victor N. Nemykin and
• Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 1854–1858, doi:10.3762/bjoc.14.159

• -iodobenzenesulfonate with Oxone or sodium periodate in water is reported. The single crystal X-ray diffraction analysis reveals a complex polymeric structure consisting of three units of IBS as potassium salt and one unit of 2-iodoxybenzenesulfonic acid linked together by relatively strong I=O···I intermolecular

• -iodosylbenzenesulfonic acid as confirmed by X-ray diffraction analysis [17]. In the present work, we report the preparation and isolation of IBS (as potassium or sodium salts) and its structural study by X-ray analysis. Furthermore, we have developed a new method for the preparation of the IBS reduced form, 2

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

• Rakesh Puttreddy,
• Ngong Kodiah Beyeh,
• S. Maryamdokht Taimoory,
• Daniel Meister,
• John F. Trant and
• Kari Rissanen

Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

• Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, N9B 3P4, Canada 10.3762/bjoc.14.146 Abstract Host–guest complexes of C-hexyl-2-bromoresorcinarene (BrC6) with twelve potential aromatic N-oxide guests were studied using single crystal X-ray diffraction analysis and

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• molecular structure of 4,5-benzotropone (11) was determined by Hata’s group [50]. X-ray diffraction analysis showed that the molecule is approximately planar and the bond alternation in the seven-membered ring and C=O bond length support satisfactory aromaticity. 2.1. Synthesis of 4,5-benzotropone (11

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• pyrenyl–thymine 2 was confirmed by single-crystal X-ray analysis. Crystal structure Crystals of 2 suitable for X-ray diffraction analysis were obtained by slow diffusion of pentane into a chloroform solution of 2. The oak ridge thermal-ellipsoid plot (ORTEP) with the atom labelling scheme is shown in

Enzymatic separation of epimeric 4-C-hydroxymethylated furanosugars: Synthesis of bicyclic nucleosides

• Neha Rana,
• Manish Kumar,
• Vinod Khatri,
• Jyotirmoy Maity and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2017, 13, 2078–2086, doi:10.3762/bjoc.13.205

• , IR spectra and HRMS) analysis. The structure of known compounds 9 [19] and 14 [20] were further confirmed on the basis of comparison of its physical and spectral data with those reported in the literature. The single crystal X-ray diffraction analysis has been performed on compounds 5, 10 and 14 and

Mechanochemical enzymatic resolution of N-benzylated-β³-amino esters

• Mario Pérez-Venegas,
• Gloria Reyes-Rangel,
• Adrián Neri,
• Jaime Escalante and
• Eusebio Juaristi

Beilstein J. Org. Chem. 2017, 13, 1728–1734, doi:10.3762/bjoc.13.167

• ); however, the best results continued to be obtained by using the conditions indicated in Table 1, entry 3. To establish the absolute configuration of product 2a, a sample was crystallized to give a suitable single-crystal for X-ray diffraction analysis. The resulting structure showed the R configuration

First total synthesis of kipukasin A

• Chuang Li,
• Haixin Ding,
• Zhizhong Ruan,
• Yirong Zhou and
• Qiang Xiao

Beilstein J. Org. Chem. 2017, 13, 855–862, doi:10.3762/bjoc.13.86

• -isopropylidene-D-ribofuranose (12) with 2-iodobenzoyl chloride (0.9 equiv) gave the corresponding 5-O-benzoyl ester 13 in 80% yield along with a small amount of the 3,5-dibenzoyl ester. The structure of 5-O-benzoyl ester 13 was unambiguously confirmed by X-ray diffraction analysis (Figure 3) [34]. Then

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• with respect to their structural and electronic properties, we herein present some relevant data of the 1,2,4-triazolium-hydrazinides 7. Thus, the molecular structure of 7a in the solid state was determined by X-ray diffraction analysis and is shown in Figure 4. Two symmetrically independent molecules

Brønsted acid-mediated cyclization–dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines

• Ramana Sreenivasa Rao and
• Chinnasamy Ramaraj Ramanathan

Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46

• evidence for cyclized compounds 9b and 10a was supported by single-crystal X-ray diffraction analysis (Figure 3) in addition to IR, NMR and HRMS data. To show the synthetic utility of substituted pyrazinones, we introduce a phenyl group at the C-3 position in pyrazinone derivative 10a. To begin with, the

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

• Dimpee Gogoi,
• Runjun Devi,
• Pallab Pahari,
• Bipul Sarma and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

• evidences for the structural assignment were sought from X-ray crystallography. Fortunately, we got the single crystals of (±)-5k by slow evaporation of a solution of 5k in hexane/EtOAc, and its molecular structure was confirmed by X-ray diffraction analysis (Figure 3). The 1H and 13C NMR spectra of all the