The polymorphism of 2-benzoyl-N,N-diethylbenzamide

The crystal structures of two new polymorphs of 2-benzoyl-N,N-diethylbenzamide were obtained after recrystallization trials with different solvents. The new forms II and III were monoclinic and crystallized in the same space group with similar a, b and c lengths but different β angles. The forms had no conformation differences within themselves; however, the long-range packing (> two unit cells) was not isostructural. In comparison with the previously published crystal structure, form I, different conformations and packing arrangements were observed. The new form II was thermally characterized and stable at room temperature, when heated up to its melting point and when cooled to −170 °C. Additionally, once form II was re-heated, a fourth form is observed after a phase transition from the monoclinic to the orthorhombic crystal systems, form IV

Direct aerobic oxidation of alcohols into esters catalyzed by carbon nanotube–gold nanohybrids

International audienceGold nanoparticles supported on carbon nanotubes were shown to efficiently catalyze the oxidation of alcohols to methyl esters under mild and selective reaction conditions. The reaction works with low catalyst loadings and the nanohybrid could be readily recycled and reused

Triphenylbismuth dichloride-mediated conversion of thioamides to nitriles

International audienc

Catalytic Dehydrosulfurization of Thioamides to Nitriles by Gold Nanoparticles Supported on Carbon Nanotubes

International audienceA gold‐carbon nanotube nanohybrid was shown to act as an efficient heterogeneous catalyst in the smooth and selective conversion of thioamides to the corresponding nitriles. The reaction was performed under mild conditions (room temperature, atmospheric pressure of oxygen) using only a gold loading of 0.35 mol %. Substituted aromatic or aliphatic nitriles were produced in very good to excellent yields and the catalyst could be easily recycled and reused over several consecutive cycles with no loss in dehydrosulfurization performances

Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement

A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported

Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement

A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported

Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement

A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported

Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement

A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported

One-Pot Regioselective Synthesis of <i>meta</i>-Terphenyls via [3 + 3] Annulation of Nitroallylic Acetates with Alkylidenemalononitriles

A highly efficient one-pot method has been developed for the synthesis of <i>meta</i>-terphenyls via a regioselective [3 + 3] annulation-elimination sequence involving Morita–Baylis–Hillman (MBH) acetates of nitroalkenes and alkylidenemalononitriles. The reaction takes place in a regioselective manner under mild conditions (Et₃N, room temperature) to afford a wide variety of <i>meta</i>-terphenyls bearing aryl, heteroaryl and styrenyl groups. This novel [3 + 3] annulation takes advantage of the 1,3-bielectrophilic character of MBH acetates and 1,3-binucleophilic character of alkylidenemalononitriles and proceeds in a cascade fashion comprising an S_N2′ substitution, intramolecular 6-<i>endo-trig</i> Michael addition and double elimination. Representative synthetic transformations of the products, for instance, to <i>meta</i>-terphenyl derived isoindolinones have also been demonstrated

Memory Effect and Crystallization of ( R ,S )-2-Chloromandelic Acid Glass

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