Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

• Awatef Ayadi,
• Aziz El Alamy,
• Olivier Alévêque,
• Magali Allain,
• Nabil Zouari,
• Mohammed Bouachrine and
• Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

• structure refinement are given in Table 1. Crystallographic data for the structural analysis have been deposited within the Cambridge Crystallographic Data Centre, CCDC 1055120 (ligand L1) and CCDC 1055119 (complex 3). Suitable single crystals for X-ray analysis have been grown for ligand L1 upon

The chemical behavior of terminally tert-butylated polyolefins

• Dagmar Klein,
• Henning Hopf,
• Peter G. Jones,
• Ina Dix and
• Ralf Hänel

Beilstein J. Org. Chem. 2015, 11, 1246–1258, doi:10.3762/bjoc.11.139

• (as well as many of their precursors) were characterized by X-ray structural analysis. These polyolefins are substructures of the most famous polyene, “polyacetylene”. Having prepared and unambiguously characterized the hydro-carbons 2, we now turn to their chemical behavior. In the sense that these

• prepare crystals of 17 suitable for an X-ray structural analysis. Interestingly, Kuhn and Winterstein in their study on the chemical behavior of α,ω-diphenyloligoenes obtained different results: for 1,4-diphenylbuta-1,3-diene, bromine addition furnished the 1,2-adduct in 95% yield [3]. As in the case of

• produced in good yield (73%). The compound could be kept at −10 °C without decomposition for considerable times and was recrystallized from pentane to provide needles "suitable" for X-ray structural analysis; its qualitative structure in the solid state is reproduced in Figure 3, but should be interpreted

New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes

• Rym Hassani,
• Mahjoub Jabli,
• Yakdhane Kacem,
• Jérôme Marrot,
• Damien Prim and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2015, 11, 1175–1186, doi:10.3762/bjoc.11.132

• structures of complexes 8 and 9. The crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Center, CCDC 1052659-1052660 for 8 and 9, respectively. Crystallographic data associated with this article can be obtained, free of charge, on application to

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• structures which are even more prominent at higher concentrations. Structural analysis by TEM revealed the presence of stable fiberlike assemblies, which can further arrange side-by-side as sheets. Thus, acylated peptides as C18-PeBGF cannot be considered as micelle forming molecules as it would be expected

Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo

• Alireza Shakoori,
• John B. Bremner,
• Mohammed K. Abdel-Hamid,
• Anthony C. Willis,
• Rachada Haritakun and
• Paul A. Keller

Beilstein J. Org. Chem. 2015, 11, 481–492, doi:10.3762/bjoc.11.54

• view. Right: NOESY correlations in support of the proposed structure (s = strong; w = weak). Structural analysis of compound 23. Left: modelled structure showing the cisoid configuration of the NH and the cinnamyl substituents. Middle: X-ray crystal structure (ball and stick representation) showing the

The preparation of new functionalized [2.2]paracyclophane derivatives with N-containing functional groups

• Henning Hopf,
• Swaminathan Vijay Narayanan and
• Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 437–445, doi:10.3762/bjoc.11.50

• ) resulted in the formation of the next higher homolog 19 (73%). Both compounds were readily characterized by their analytical data (see Supporting Information File 1) and also by an X-ray structural analysis of 18. Several features are common to all structures presented in this paper. The usual features of

• characterized by their spectroscopic data (Supporting Information File 1), and for 22 we could additionally determine the solid-state structure by X-ray structural analysis (Figure 4a). The orientation of the side chains in 22 is described by the torsion angles C14–C15–N1–C17 131.2(2)°, C15–N1–C17–O −1.3(2

• most other acyl chlorides, 26 is a stable compound with a high melting point (210 °C), which could easily be recrystallized from dichloromethane/pentane to furnish single crystals suitable for X-structural analysis. The molecule of 26 (Figure 5) possesses crystallographic inversion symmetry, consistent

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• packing is shown in Figure 7. The complex units pack in a head-to-tail manner in columns parallel to the crystal b-axis. Columns of complex units A propagate as rows parallel to the a-axis, alternating with analogous columns of B complex units. Structural analysis of the inclusion complex between

Modification of physical properties of poly(L-lactic acid) by addition of methyl-β-cyclodextrin

• Toshiyuki Suzuki,
• Ayaka Ei,
• Yoshihisa Takada,
• Hiroki Uehara,
• Takeshi Yamanobe and
• Keiko Takahashi

Beilstein J. Org. Chem. 2014, 10, 2997–3006, doi:10.3762/bjoc.10.318

• other hand, Raman spectroscopy reveals the vibrational states of functional groups, but not thermal properties because irradiation affects the sample temperature [38]. For exact and expeditious structural analysis, it is important to determine simultaneously the thermal properties and the local

Five-membered ring annelation in [2.2]paracyclophanes by aldol condensation

• Henning Hopf,
• Swaminathan Vijay Narayanan and
• Peter G. Jones

Beilstein J. Org. Chem. 2014, 10, 2021–2026, doi:10.3762/bjoc.10.210

• -38106 Braunschweig, Germany 10.3762/bjoc.10.210 Abstract Under basic conditions 4,5,12,13-tetraacetyl[2.2]paracyclophane (9) cyclizes by a double aldol condensation to provide the two aldols 12 and 15 in a 3:7 ratio. The structures of these compounds were obtained from X-ray structural analysis

• deuteriochloroform) that combine to form a complex three-dimensional pattern (Table 1). Several attempts to obtain crystals of the major isomer 15 suitable for X-ray analysis failed. The anti-orientation of the carbonyl groups of compound 15 was proved by the X-ray structural analysis of the product resulting from a

Building complex carbon skeletons with ethynyl[2.2]paracyclophanes

• Ina Dix,
• Lidija Bondarenko,
• Peter G. Jones,
• Thomas Oeser and
• Henning Hopf

Beilstein J. Org. Chem. 2014, 10, 2013–2020, doi:10.3762/bjoc.10.209

• their usual spectroscopic and analytical data, the new cyclophanes 11, 12, 19, 20, 22, and 26 were characterized by X-ray structural analysis. Keywords: carbon-rich molecules; complex carbon scaffolds; cyclophanes; Glaser coupling; multibridged cyclophanes; X-ray analysis; Introduction Several years

• recrystallized to provide single crystals suitable for X-ray structural analysis. Figure 1 shows that dimer 11 indeed possesses the “crossed” structure; it crystallizes with imposed twofold symmetry, but the effective (non-crystallographic) symmetry is the unusual D2 (222) with r.m.s. deviation 0.01 Å. Despite

Structure/affinity studies in the bicyclo-DNA series: Synthesis and properties of oligonucleotides containing bc^en-T and iso-tricyclo-T nucleosides

• Branislav Dugovic,
• Michael Wagner and
• Christian J. Leumann

Beilstein J. Org. Chem. 2014, 10, 1840–1847, doi:10.3762/bjoc.10.194

• -DNA molecular platform. In both modifications the torsion around C6’–C7’ within the carbocyclic ring is planarized by either the presence of a C6’–C7’ double bond or a cyclopropane ring. Structural analysis of these two nucleosides by X-ray analysis reveals a clear preference of torsion angle γ for

Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

• Marina Rubina,
• William M. Sherrill,
• Alexey Yu. Barkov and
• Michael Rubin

Beilstein J. Org. Chem. 2014, 10, 1536–1548, doi:10.3762/bjoc.10.158

• -Bu substituent in the dihydrooxazole ring of the ligand resulted in a reversal of enantioselectivity. Such an unexpected change in the catalyst selectivity motivated us to perform structural analysis of the key intermediate complexes invoked in the catalytic cycle of the Heck arylation. First, we

Intermediates in monensin biosynthesis: A late step in biosynthesis of the polyether ionophore monensin is crucial for the integrity of cation binding

• Wolfgang Hüttel,
• Jonathan B. Spencer and
• Peter F. Leadlay

Beilstein J. Org. Chem. 2014, 10, 361–368, doi:10.3762/bjoc.10.34

• crystallised as their monosodium salts from an isohexane/ethyl acetate mixture and single crystals were subjected to X-ray structural analysis (Figure 2). Dehydroxydemethylmonensin A did not form crystals under any conditions tested. When the demethylmonensin A structure is overlaid on the structure of the

Modulating NHC catalysis with fluorine

• Yannick P. Rey and
• Ryan Gilmour

Beilstein J. Org. Chem. 2013, 9, 2812–2820, doi:10.3762/bjoc.9.316

• catalyst 10 (Scheme 3; lower) was prepared in a short synthesis starting from the primary bromide 23 [22]. Hydrogenolysis (24, 67%) [41] and subsequent conversion to the triazolium salt completed the short synthesis (52% over 3 steps). X-Ray structural analysis of 5, 6 and 7 The X-ray crystal structures of

Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin

• John Li,
• May May Leong,
• Alastair Stewart and
• Mark A. Rizzacasa

Beilstein J. Org. Chem. 2013, 9, 2762–2766, doi:10.3762/bjoc.9.310

• ], which are derivatives of docosahexaenoic acid (DHA) (Figure 1) and the E-series [4] derived from eicosapentaenoic acid. Structural analysis by mass spectrometry (MS) showed that resolvin D2 (RvD2, 1) was a 17-hydroxy derivative of DHA (17HDHA) [1]. However, no NMR experiments were performed due to

Micro-flow synthesis and structural analysis of sterically crowded diimine ligands with five aryl rings

• Shinichiro Fuse,
• Nobutake Tanabe,
• Akio Tannna,
• Yohei Konishi and
• Takashi Takahashi

Beilstein J. Org. Chem. 2013, 9, 2336–2343, doi:10.3762/bjoc.9.268

• detailed structural study. Herein, we report an efficient micro-flow synthesis and structural analysis of sterically crowded 1,2,3,4,5-pentaaryl-1,3,5-triazapenta-1,4-diene ligands 3b and 3c, and their use in the copolymerization of ethylene and polar monomers. According to the previous report, 1,2,3,4,5

Self-assembly of 2,3-dihydroxycholestane steroids into supramolecular organogels as a soft template for the in-situ generation of silicate nanomaterials

• Valeria C. Edelsztein,
• Andrea S. Mac Cormack,
• Matías Ciarlantini and
• Pablo H. Di Chenna

Beilstein J. Org. Chem. 2013, 9, 1826–1836, doi:10.3762/bjoc.9.213

• of the steroid. A structural analysis of the steroids 2, 3 and 4, with hydroxy groups at equatorial positions, showed that angles and distances between the hydroxy groups are inadequate to give the intermolecular hydrogen bonding necessary for the one-dimensional self-assembly. These results led to

The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives

• André S. Kelch,
• Peter G. Jones,
• Ina Dix and
• Henning Hopf

Beilstein J. Org. Chem. 2013, 9, 1705–1712, doi:10.3762/bjoc.9.195

• with various bromination reagents. Whenever possible we confirm the structures of intermediate compounds or byproducts by X-ray structural analysis. Results and Discussion cis,cis,cis,cis-1,2,3,4,5-Pentakis(hydroxymethyl)cyclopentane (16) and derivatives The pentaalcohol 16 is a known compound, having

• silica gel, the main isomer began to crystallize partially from the highly viscous hydrogenation mixture after standing for several months. The crystals obtained were suitable for X-ray structural analysis, which showed that this isomer has the cis,cis,cis,trans-geometry, i.e. 26 (Figure 3). The

• the best results. Under these conditions the hexabromide 32 was produced in 45% yield. The structure of this cyclopentadiene derivative was derived from its spectroscopic data (see Supporting Information File 1) and also by an X-ray structural analysis (Figure 4). A rationalization of the route from 8

Isolation and X-ray characterization of palladium–N complexes in the guanylation of aromatic amines. Mechanistic implications

• Abdessamad Grirrane,
• Hermenegildo Garcia and
• Eleuterio Álvarez

Beilstein J. Org. Chem. 2013, 9, 1455–1462, doi:10.3762/bjoc.9.165

• complexes of the type of bis(guanidino)Pd(II) (4a–c) (Scheme 2) whose structures have been characterized by single-crystal X-ray structural analysis, as well as to obtain evidence for the intermediacy of these complexes in the catalytic process. Overall the present data reinforce the previous proposal for

Dipolar addition to cyclic vinyl sulfones leading to dual conformation tricycles

• Steven S. Y. Wong,
• Michael G. Brant,
• Christopher Barr,
• Allen G. Oliver and
• Jeremy E. Wulff

Beilstein J. Org. Chem. 2013, 9, 1419–1425, doi:10.3762/bjoc.9.159

• the regio- and stereochemical outcome of the cycloaddition as that indicated for structure 3. This structural analysis was subsequently confirmed by X-ray crystallographic analysis of 3a (Figure 1) [36]. Further VT NMR studies of 3a in CDCl3 (Figure 2B) revealed a substantial broadening of several key

A new synthetic access to 2-N-(glycosyl)thiosemicarbazides from 3-N-(glycosyl)oxadiazolinethiones and the regioselectivity of the glycosylation of their oxadiazolinethione precursors

• El Sayed H. El Ashry,
• El Sayed H. El Tamany,
• Mohy El Din Abdel Fattah,
• Mohamed R. E. Aly,
• Ahmed T. A. Boraei and
• Axel Duerkop

Beilstein J. Org. Chem. 2013, 9, 135–146, doi:10.3762/bjoc.9.16

• -N-(glucosyl)- and (galactosyl)oxadiazolinethiones. Crystal data, instrumental and refinement data for 23. Crystal data, instrumental and refinement data for 29. Crystal data, instrumental and refinement data for 30. Supporting Information Complete crystallographic data of the structural analysis of

Total synthesis and biological evaluation of fluorinated cryptophycins

• Christine Weiß,
• Tobias Bogner,
• Benedikt Sammet and
• Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 2060–2066, doi:10.3762/bjoc.8.231

• cryptophycin-1 from the related Nostoc strain GSV 224, investigated the stereochemistry, and described the cytotoxicity [2]. At the same time Kobayashi et al. succeeded in a full structural analysis and described the first total synthesis of another member of the cryptophycin family [3][4]. Twenty-eight

The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

Self-assembled organic–inorganic magnetic hybrid adsorbent ferrite based on cyclodextrin nanoparticles

• Ângelo M. L. Denadai,
• Frederico B. De Sousa,
• Joel J. Passos,
• Fernando C. Guatimosim,
• Kirla D. Barbosa,
• Ana E. Burgos,
• Fernando Castro de Oliveira,
• Jeann C. da Silva,
• Bernardo R. A. Neves,
• Nelcy D. S. Mohallem and
• Rubén D. Sinisterra

Beilstein J. Org. Chem. 2012, 8, 1867–1876, doi:10.3762/bjoc.8.215

• in the solid state and in aqueous suspension, and their properties were compared with pure ferrite. Structural analysis pointed out that the synthesis approach was able to incorporate βCD in the ferrite matrix, which allowed us to keep the important βCD characteristics in the final magnetic material

Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

• Jan Hoyer,
• Ulrich Schatzschneider,
• Michaela Schulz-Siegmund and
• Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

• -butyloxycarbonyl (Boc). Indeed, we did not observe concomitant deprotection of lysine side chains, which was favored by the fact that Mtt groups situated at the N-terminus are even more acid-sensitive than Nε-Mtt groups [25]. The structural analysis of the (sC18)2 conjugates by circular dichroism spectroscopy did