Synthesis of axially chiral oxazoline–carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe₂

• Feijun Wang,
• Shengke Li,
• Mingliang Qu,
• Mei-Xin Zhao,
• Lian-Jun Liu and
• Min Shi

Beilstein J. Org. Chem. 2012, 8, 726–731, doi:10.3762/bjoc.8.81

• its structure was established by single-crystal X-ray diffraction studies (Figure 4; Supporting Information File 2). The crystal data of Au(1)–C(7) (1.991(5) Å) is a typical Au–CNHC bond length, in-line with those of other reported examples [16][17][18][19][20][21]. Furthermore, the angle of I(1)–Au(1

Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles

• Pavol Jakubec,
• Dane M. Cockfield,
• Madeleine Helliwell,
• James Raftery and
• Darren J. Dixon

Beilstein J. Org. Chem. 2012, 8, 567–578, doi:10.3762/bjoc.8.64

• followed by single-crystal X-ray diffraction studies of both isomers allowed unambiguous determination of the relative stereochemical configurations in each case. For more details of the elucidation of the relative configuration see Supporting Information File 1. The products were epimeric only at the

• –c to LiAlH4 in THF followed by quenching and treatment with HCOOH, spirocycles 11a–c were obtained in good yields. The chemoselectivity of the reduction was unambiguously confirmed by single-crystal X-ray diffraction studies of 11c. Furthermore, the use of an excess of DIBAL at room temperature

Self-assembly of Ru₄ and Ru₈ assemblies by coordination using organometallic Ru(II)₂ precursors: Synthesis, characterization and properties

• Sankarasekaran Shanmugaraju,
• Dipak Samanta and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2012, 8, 313–322, doi:10.3762/bjoc.8.34

• salts in high yields and were characterized fully by multinuclear (1H, 13C and 19F) NMR, infrared (IR) and electrospray ionization mass spectrometry (ESIMS). In addition, the molecular structure of macrocycle 2a was established unequivocally by single-crystal X-ray diffraction analysis and adopts a

• molecular structure of the tetranuclear metallamacrocycle [(p-cymene)4Ru4(μ-η4-oxalato)2(L)]4+(O3SCF3−)4 (2a) was unambiguously determined by single-crystal X-ray diffraction analysis. Single crystals of 2a of high enough quality for X-ray diffraction were grown by slow vapor diffusion of diethyl ether into

• -crystal X-ray diffraction analysis, which reveals a tetranuclear geometry with the dimensions of 5.53 Å × 12.39 Å. In addition to their synthesis and characterization, the UV–vis absorption and cyclic voltammetry studies are reported. Results and Discussion Synthesis and characterization of the

A ferrocene redox-active triazolium macrocycle that binds and senses chloride

• Nicholas G. White and
• Paul D. Beer

Beilstein J. Org. Chem. 2012, 8, 246–252, doi:10.3762/bjoc.8.25

• , 597.2239. X-ray crystallography Single crystal X-ray diffraction data for 3 were collected by using synchrotron radiation (λ = 0.6889 Å) at the Diamond Light Source, Beam I19. The diffractometer was equipped with a Cryostream N2 open-flow cooling device [19] and the data were collected at 100(2) K. A

Regioselectivity in the multicomponent reaction of 5-aminopyrazoles, cyclic 1,3-diketones and dimethylformamide dimethylacetal under controlled microwave heating

• Kamal Usef Sadek,
• Ramadan Ahmed Mekheimer,
• Tahany Mahmoud Mohamed,
• Moustafa Sherief Moustafa and
• Mohamed Hilmy Elnagdi

Beilstein J. Org. Chem. 2012, 8, 18–24, doi:10.3762/bjoc.8.3

• single-crystal X-ray diffraction [25][26] (Figure 1, Figure 2 and Table 1, Table 2, Table 3). With this result in hand, we went on to study the scope of such multicomponent reactions with several substituted 5-aminopyrazoles and cyclic 1,3-diketones. Thus, the reaction of 1b–f with 2a,b and 3, under the

• established by single-crystal X-ray diffraction of compounds 6e,g (Figure 3, Figure 4 and Table 3, Table 4) [27][28]. A proposed mechanism to account for the formation of products 6 is illustrated in Scheme 2. The base-catalyzed reaction of cyclic 1,3-diketones 2 with DMFDMA 3 gave the enaminone 7, which

Efficient synthesis of 1,3-diaryl-4-halo-1H-pyrazoles from 3-arylsydnones and 2-aryl-1,1-dihalo-1-alkenes

• Yiwen Yang,
• Chunxiang Kuang,
• Hui Jin,
• Qing Yang and
• Zhongkui Zhang

Beilstein J. Org. Chem. 2011, 7, 1656–1662, doi:10.3762/bjoc.7.195

• pyrazole 3g was further confirmed by single-crystal X-ray diffraction studies (Figure 1). In order to elucidate the probable reaction mechanism, a mixture of 1a, 2a and xylene was stirred in the dark at 160 °C. After 16 h, no product was found. The results indicate that it was difficult for 2-aryl-1,1

NMR studies of anion-induced conformational changes in diindolylureas and diindolylthioureas

• Damjan Makuc,
• Jennifer R. Hiscock,
• Mark E. Light,
• Philip A. Gale and
• Janez Plavec

Beilstein J. Org. Chem. 2011, 7, 1205–1214, doi:10.3762/bjoc.7.140

• systems to adopt a planar conformation. Whilst the conformational properties of these compounds have been explored by single crystal X-ray diffraction in the solid-state, a detailed analysis of the conformational properties of the these compounds in solution, in the absence and presence of oxo-anions, has

Intraannular photoreactions in pseudo-geminally substituted [2.2]paracyclophanes

• Henning Hopf,
• Vitaly Raev and
• Peter G. Jones

Beilstein J. Org. Chem. 2011, 7, 658–667, doi:10.3762/bjoc.7.78

• cyclooctadienes were not separated from each other. Fractional crystallization of the mixture of cyclooctadienes from CHCl3/MeOH mixture gave an analytically pure sample of 13, which was characterized by single-crystal X-ray diffraction (Figure 1). Further irradiation of compounds 13, 14 and 15 did not lead to

A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative

• Zhipei Yang,
• Kai Zhang,
• Fangbin Gong,
• Shayu Li,
• Jun Chen,
• Jin Shi Ma,
• Lyubov N. Sobenina,
• Albina I. Mikhaleva,
• Guoqiang Yang and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2011, 7, 46–52, doi:10.3762/bjoc.7.8

• description of the synthesis of receptor 1 has been reported [5]. Crystals of receptor 1 suitable for analysis by single crystal X-ray diffraction were obtained by recrystallization from CH3CN. Methods. UV–vis absorption spectra were recorded on a Hitachi U-3010 spectrophotometer. Fluorescence spectra were

Chiral gels derived from secondary ammonium salts of (1R,3S)-(+)-camphoric acid

• Tapas Kumar Adalder,
• N. N. Adarsh,
• Ravish Sankolli and
• Parthasarathi Dastidar

Beilstein J. Org. Chem. 2010, 6, 848–858, doi:10.3762/bjoc.6.100

• powder X-ray diffraction. Structure property correlation based on X-ray diffraction techniques remain inconclusive indicating that some of the integrated part associated with the gelation phenomena requires a better understanding. Keywords: crystal engineering; LMOG; single crystal X-ray diffraction

• crystallize as many salts as possible. However, our best efforts resulted in the crystallization of only three salts, DBUAMC 3, DBAMC 6 and DCHADC 1, which were examined by single crystal X-ray diffraction (Table 2). The crystal of DBUAMC 3 isolated from ethylene glycol/methanol mixture belongs to the

• to the formation of a 3-D hydrogen bonded network (Figure 5). Crystals of DBAMC 6 suitable for single crystal X-ray diffraction study were grown from mesitylene. It crystallized in the non-centrosymmetric monoclinic space group P21. The C–O distances of the carboxylic acid moieties are 1.237(2)–1.270

Synthesis of oxa-bridged derivatives from Diels–Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

• Faiz Ahmed Khan and
• Karuppasamy Parasuraman

Beilstein J. Org. Chem. 2010, 6, No. 64, doi:10.3762/bjoc.6.64

• )” [16]. In our reinvestigation we used 3-sulfolene as a 1,3-butadiene source to prepare both the mono- and bis-adducts. The two diastereomeric bis-adducts were separated and the relative stereochemistry was established by single crystal X-ray diffraction and 1H NMR spectroscopy. The bis-adducts were

• bis-oxa-bridged compounds. The relative stereochemistry of the products was unambiguously established by single crystal X-ray diffraction and NMR spectroscopy. ORTEP structure of 8 [50% probability thermal ellipsoids; some of the hydrogen atoms and a solvent molecule (acetonitrile) are omitted for

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

• Bruno Linclau,
• Leo Leung,
• Jean Nonnenmacher and
• Graham Tizzard

Beilstein J. Org. Chem. 2010, 6, No. 62, doi:10.3762/bjoc.6.62

• combination (Scheme 3), the defluorinated reaction products 13 and 14 were obtained. We have not yet deduced an acceptable explanation for this unexpected result. Crystallographic analysis Compounds 7 and 3 yielded colourless crystals suitable for study by single crystal X-ray diffraction [48]. The dibenzyl

Acid catalyzed cyclodimerization of 2,2-bis(trifluoromethyl)-4-alkoxy-oxetanes and -thietanes. Synthesis of 2,2,6,6-tetrakis(trifluoromethyl)-4,8-dialkoxy-1,5-dioxocanes and 3,3,7,7-tetrakis(trifluoromethyl)-9-oxa-2,6-dithia-bicyclo[3.3.1]nonane

• Viacheslav A. Petrov and
• Will Marshall

Beilstein J. Org. Chem. 2010, 6, No. 46, doi:10.3762/bjoc.6.46

• -dioxocanes, isolated in 31–42% yield. The structures of two products (R = C2H5O and n-C3H7O) were established by single crystal X-ray diffraction. The corresponding oxetane carrying the bulky t-C4H9O group has different reactivity towards BF3·OEt2, slowly producing a mixture of two acyclic, unsaturated

• was established by single crystal X-ray diffraction. Keywords: cyclodimerization; electrophilic [4 + 4] cyclodimerization; fluorinated oxetanes; fluorinated thietanes; reaction with alcohols; reaction with H2SO4; Introduction Polyfluorinated 2,2-bis(trifluoromethyl)-4-alkoxy-oxetanes and -thietanes

• , Table 1, Entries 1, 2) and starting oxetanes 1a, b have a similar appearance, spectroscopic data were not sufficient for an unambiguous assignment of the structure. Consequently, structure assignments for 2a and 2b were made based on single crystal X-ray diffraction data (see Supporting Information File

Synthesis and binding studies of two new macrocyclic receptors for the stereoselective recognition of dipeptides

• Ana Maria Castilla,
• M. Morgan Conn and
• Pablo Ballester

Beilstein J. Org. Chem. 2010, 6, No. 5, doi:10.3762/bjoc.6.5

• the formation of the peptide bonds of the macrocyclic structures, both receptors have been isolated as single diastereoisomers. The molecular structure of receptor 1 has been confirmed by single-crystal X-ray diffraction analysis. Although molecular modeling suggested that the cyclic receptors can

The subtle balance of weak supramolecular interactions: The hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts

• Kari Raatikainen,
• Massimo Cametti and
• Kari Rissanen

Beilstein J. Org. Chem. 2010, 6, No. 4, doi:10.3762/bjoc.6.4

• -ClPhNH3H2PO4 (8), 3-IPyBnCl (9), 3-IPyHCl (10) and 3-IPyH-5NIPA (3-iodopyridinium 5-nitroisophthalate, 13), where hydrogen or/and halogen bonding represents the most relevant non-covalent interactions, has been prepared and characterized by single crystal X-ray diffraction. This series was further complemented

Functional properties of metallomesogens modulated by molecular and supramolecular exotic arrangements

• Alessandra Crispini,
• Mauro Ghedini and
• Daniela Pucci

Beilstein J. Org. Chem. 2009, 5, No. 54, doi:10.3762/bjoc.5.54

• intermolecular interactions in the crystalline organization grafted around the gallium(III) centre [61]. In this way a unconventional jellyfish shape molecule has been obtained and its molecular structure has been confirmed through single crystal X-ray diffraction (Figure 6). Despite its unusual molecular shape

A facile synthesis and fungicidal activities of 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin- 4(3H)-ones

• Yang-Gen Hu,
• Ai-Hua Zheng,
• Xu-Zhi Ruan and
• Ming-Wu Ding

Beilstein J. Org. Chem. 2008, 4, No. 49, doi:10.3762/bjoc.4.49

• -d]pyrimidin-4(3H)-ones 6 and 8 in satisfactory yield. Their structures were confirmed by 1H NMR, EI-MS, IR and elementary analysis, and compound 8c was further analyzed by single-crystal X-ray diffraction. The preliminary bioassays indicated that these compounds showed excellent fungicidal

Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine

• Annabella F. Newton,
• Martin Rejzek,
• Marie-Lyne Alcaraz and
• Robert A. Stockman

Beilstein J. Org. Chem. 2008, 4, No. 4, doi:10.1186/1860-5397-4-4

• isolated from a ladybird beetle Hippodamia convergens by Tursch and co-workers in 1972 [3]. The structure of hippodamine (1) was established two years later by the same group [4] on the basis of a single-crystal X-ray diffraction experiment (Figure 1). Epi-hippodamine (2) is its unnatural isomer with an