Large-Scale Carbonyl Reductions in the Pharmaceutical Industry

The present invention relates to compounds of the formula (I) and to the use thereof in organic electronic devices, and to organic electronic devices which comprise compounds of the formula (I), preferably as hole-transport materials and/or as matrix materials, in particular in combination with a further matrix material.

Compounds for electronic devices

Elemental sulfur has been known since Antiquity and found widespread applications in the preparation of black gunpowder, the synthesis of sulfuric acid as well as other sulfur-containing compounds, and the vulcanization of rubber. Over the last several years, we have come to better understand its properties and discover more applications of elemental sulfur in synthetic organic chemistry. This review summarizes the advances from 2000 in the construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.

Recent Advances in Organic Reactions Involving Elemental Sulfur

III. Structures of Organic Polysulfanes 3922 A. General 3922 B. Structures of Chain-Like R−Sn−R Molecules 3923 C. Structures of Cyclic R−Sn−R Molecules 3924 D. Conformational Studies 3925 IV. Analysis of Organic Polysulfanes 3925 A. General 3925 B. NMR Spectroscopy 3926 C. Chromatography 3926 D. Raman Spectroscopy 3928 E. XANES Spectroscopy 3928 V. Reactions of Organic Polysulfanes 3928 A. Interconversion Reactions 3928 B. Sulfur Transfer Reactions 3930 C. Replacement Reactions 3931 D. Nucleophilic Displacement Reactions at the Sulfur−Sulfur Bond 3931

The chemistry of organic polysulfanes R-Sn-R (n > 2)

A novel multicomponent synthesis of 5-aminooxazole starting from simple and readily available inputs is described Thus, simply heating a methanol solution of an aldehyde 3, an amine 4, and an α-isocyanoacetamide 5 provided the 5-aminooxazole (1) in good to excellent yield The reaction of 1 with α,β-unsaturated acyl chloride 13 lead to the formation of pyrrolo[3,4-b]pyridin-5-one (2) in a single operation A triple domino sequence, acylation/IMDA/retro-Michael cycloreversion, is involved in this new scaffold-generating reaction After the observation that ammonium chloride can significantly accelerate the oxazole formation in toluene, a one-pot four-component synthesis of 2 is developed

Ammonium Chloride-Promoted Four-Component Synthesis of Pyrrolo[3,4-b]pyridin-5-one

First direct synthesis of 4,8-dialkylbenzo[1,2-d;4,5-d′]bis[1,2,3]trithioles and 6,10-dialkyl[1,2,3]trithiolo[5,4-h]benzopentathiepins from 1,4-dialkyl-2,3,5,6-tetrabromobenzenes

Synthesis and reactions of new cyclic polysulfides. 6,10-Disubstituted[1,2,3]trithiolo[5,4-h]benzopentathiepins

Many cyclic polysulfides, i.e., benzopentathiepins (3a–d), 6H-1,2,3,4,5-benzopentathiocin, 5H-1,2,3,4-benzotetrathiepin, 3H-1,2-benzodithiole, 1,5-dihydro-2,3,4-benzotrithiepin, 1,4-dihydro-2,3-benzodithiin, naphtho[1,8-cd]-1,2-dithiole, 1,2,3-trithiane, 1,2-dithiane, 2,3,4,5-tetrathiabicyclo[4.4.0]decane, and 2,3,4,5,6-pentathiabicyclo[5.4.0]undecane, were synthesized in high yields by new reactions of their corresponding dithiols and related compounds, 1,3-benzodithiole-2-thiones (5) and 1,3-dithiolane-2-thione, with elemental sulfur in liquid ammonia at ambient temperature. In the synthesis of 3a–d from 1,2-benzenedithiol or 5, considerable increase in the product yield was observed upon adding 1,3-dinitrobenzene to the solvent used in work-up.

Synthesis of cyclic polysulfides. Reactions of dithiols and related compounds with elemental sulfur in liquid ammonia

Benzopentathiepins were synthesized by new reaction of 1,3-benzodithiole-2-thiones and 1,2-benzenedithiols with elemental sulfur/liquid ammonia at ambient temperature in high yields.

Synthesis of benzopentathiepins. reactions of 1,3-benzodithiole-2-thione and 1,2-benzenedithiol with elemental sulfur in liquid ammonia

Benzopentathiepin (BPT) reacted with many aromatic compounds such as benzene, 1,4-dimethylbenzene, and naphthalene in the presence of Lewis acid to give various thianthrenes in moderate yields. BPT was found to serve as a 1,4-dication synthon

Takehiko Goto

Papers

First direct synthesis of 4,8-dialkylbenzo[1,2-d;4,5-d′]bis[1,2,3]trithioles and 6,10-dialkyl[1,2,3]trithiolo[5,4-h]benzopentathiepins from 1,4-dialkyl-2,3,5,6-tetrabromobenzenes

Synthesis and reactions of new cyclic polysulfides. 6,10-Disubstituted[1,2,3]trithiolo[5,4-h]benzopentathiepins

Synthesis of cyclic polysulfides. Reactions of dithiols and related compounds with elemental sulfur in liquid ammonia

Synthesis of benzopentathiepins. reactions of 1,3-benzodithiole-2-thione and 1,2-benzenedithiol with elemental sulfur in liquid ammonia

Chemistry on benzopentathiepin: reactions of benzopentathiepin with aromatic compounds in the presence of Lewis acid