New developments in gold-catalyzed manipulation of inactivated alkenes

• Michel Chiarucci and
• Marco Bandini

Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294

• obtained from moderate to good yields under microwave irradiation (DCE, Scheme 17c) [54]. Additionally, the stronger Lewis acid AuCl3/AgSbF6 was documented to catalyze the Markovnikov selective hydroarylation of aryl- and alkyl olefins with less-nucleophilic benzene derivatives and thiophene in good yields

• indoles to alkenes. Intermolecular [Au(III)]-catalyzed hydroarylation of alkenes with benzene derivatives and thiophene. a) Intramolecular [Au(III)]-catalyzed hydroarylation of alkenes. b) A SEAr-type mechanism was hypothesized by the authors. Intramolecular [Au(I)]-catalyzed hydroalkylation of alkenes

Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes

• Ana M. Sanjuán,
• Alberto Martínez,
• Patricia García-García,
• Manuel A. Fernández-Rodríguez and
• Roberto Sanz

Beilstein J. Org. Chem. 2013, 9, 2242–2249, doi:10.3762/bjoc.9.263

• presence of cationic gold(I) complexes instead of the usually more favoured 5-exo-dig pathway. So, we initially prepared a variety of these o-disubstituted benzene derivatives 1 by two approaches (see Supporting Information File 1) (Scheme 3). First, o-(bromo)-3-(methylbut-2-enyl)benzene was prepared by

The first example of the Fischer–Hepp type rearrangement in pyrimidines

• Inga Cikotiene,
• Mantas Jonusis and
• Virginija Jakubkiene

Beilstein J. Org. Chem. 2013, 9, 1819–1825, doi:10.3762/bjoc.9.212

• presence of a group with a positive mesomeric effect in position 2 of the pirimidine ring is crucial for the migration of the nitroso group to C-5. The migration of a nitroso group in benzene derivatives is a well-known reaction, named Fischer–Hepp rearrangement (Scheme 5) [40][41][42]. The classical

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

• Sophie Fourmentin,
• Anca Ciobanu,
• David Landy and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1185–1191, doi:10.3762/bjoc.9.133

• benzenes (Figure 2) was selected in analogy to the corresponding benzoates investigated previously [3]. These benzene derivatives were equilibrated in seated vials at very low concentrations (1 ppm) with solutions of β-CD derivatives (concentrations 1–10 mM). The partial pressures of these guests in the

• corresponding cyclohexane derivatives showed indeed a slope similar to the benzene derivatives, but free enthalpies more negative by ΔΔG°= 2 kJ mol−1, which was attributed to the larger diameter of cyclohexane compared to benzene filling the β-CD cavity more completely. For taking the space filling of the CD

• cavity 262 Å3 [41], which means that the β-CD cavity within host 4, extended by the thioether substituents, is nearly completely occupied by it. The ability of the program Macromodel (from Schrödinger Inc.) to predict the nonpolar interactions between host 4 and benzene derivatives was finally evaluated

Synthesis of SF₅-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes

• Petr Beier and
• Tereza Pastýříková

Beilstein J. Org. Chem. 2013, 9, 411–416, doi:10.3762/bjoc.9.43

• [26] nucleophiles, and oxidative nucleophilic substitution of hydrogen (ONSH) with Grignard and organolithium reagents [27]. This chemistry significantly expanded the range of available SF5-benzene derivatives. The synthetic chemistry and biological activity of pentafluorosulfanyl organic molecules

The β-cyclodextrin/benzene complex and its hydrogen bonds – a theoretical study using molecular dynamics, quantum mechanics and COSMO-RS

• Jutta Erika Helga Köhler and
• Nicole Grczelschak-Mick

Beilstein J. Org. Chem. 2013, 9, 118–134, doi:10.3762/bjoc.9.15

• shows multiple topologies/configurations (guest up/down) in MD with λ-dynamics [14]. The association constant Ka for α- and β-CD inclusion complexes with several benzene derivatives was investigated by a genetic algorithm [15] and neuronal networks [16]. An overview of quantum mechanical methods to

The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

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

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• bridging C–C bond and a formal [1,2]-alkynyl shift. Li et al. reported the first gold-catalyzed reaction of propargylcyclopropene systems 212 which affords benzene derivatives 213 in high yields [94] (Scheme 39). Only few efficient methods have emerged for the synthesis of cyclobutane derivatives, which

The arene–alkene photocycloaddition

• Ursula Streit and
• Christian G. Bochet

Beilstein J. Org. Chem. 2011, 7, 525–542, doi:10.3762/bjoc.7.61

• Ursula Streit Christian G. Bochet Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland 10.3762/bjoc.7.61 Abstract In the presence of an alkene, three different modes of photocycloaddition with benzene derivatives can occur; the [2 + 2] or ortho, the [3

• + 2] or meta, and the [4 + 2] or para photocycloaddition. This short review aims to demonstrate the synthetic power of these photocycloadditions. Keywords: benzene derivatives; cycloadditions; Diels–Alder; photochemistry; Introduction Photocycloadditions occur in a variety of modes [1]. The best

• benzvalene [2][3] and fulvene when excited to its first excited-state, or to Dewar benzene [4][5] via excitation to its second excited-state (Scheme 1) [6]. In the presence of an alkene, three different modes of photocycloaddition with benzene derivatives can occur, viz. the [2 + 2] or ortho, the [3 + 2] or

Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

• Filipe Vilela,
• Peter J. Skabara,
• Christopher R. Mason,
• Thomas D. J. Westgate,
• Asun Luquin,
• Simon J. Coles and
• Michael B. Hursthouse

Beilstein J. Org. Chem. 2010, 6, 1002–1014, doi:10.3762/bjoc.6.113

• of this new rearrangement process, we carried out studies on analogous benzene derivatives (17, Figure 2). In each case, the addition of perchloric acid resulted in a complex mixture of products, which could not be easily separated [4]. The 1,4-aryl shift was also attempted on compound 19 to

Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues

• Aleksandra Jankowiak,
• Piotr Kaszynski,
• William R. Tilford,
• Kiminori Ohta,
• Adam Januszko,
• Takashi Nagamine and
• Yasuyuki Endo

Beilstein J. Org. Chem. 2009, 5, No. 83, doi:10.3762/bjoc.5.83

• of compounds. The lines are guides for the eye. The change in the clearing temperature ΔTc upon replacing of the –OCH2– connecting group with another in selected pairs of compounds. The lines are guides for the eye. Equilibrium ground state geometries (B3LYP/6-31G(d)) for benzene derivatives

New diarylmethanofullerene derivatives and their properties for organic thin- film solar cells

• Daisuke Sukeguchi,
• Surya Prakash Singh,
• Mamidi Ramesh Reddy,
• Hideyuki Yoshiyama,
• Rakesh A. Afre,
• Yasuhiko Hayashi,
• Hiroki Inukai,
• Tetsuo Soga,
• Shuichi Nakamura,
• Norio Shibata and
• Takeshi Toru

Beilstein J. Org. Chem. 2009, 5, No. 7, doi:10.3762/bjoc.5.7

• heterojunction thin film. Synthesis of diarylmethanofullerene derivatives Diarylmethanofullerene derivatives were synthesized according to the method cited in the literature [26]. Synthetic routes are shown in Scheme 1. Generally, the Friedel–Crafts acylation of benzene derivatives 10–14 with acid chlorides 3–9