Crystal structures of dibenzo[ce]‐1,2‐dithiine and its related oxides

The X‐ray structures of dibenzo[ce]‐1,2‐dithiine, dibenzo[ce]‐1,2‐dithiine‐5,5‐dioxide, diben‐ zo[ce]‐1,2‐dithiine‐5,5,6‐trioxide, and dibenzo[ce]‐1, 2‐dithiine‐5,5,6,6‐tetraoxide are reported and compared with the related “constrained'' naphthalene deri‐ vatives. The S‐S distances vary upon oxidation of the S centers in the order S‐S < SO‐S > SO₂‐S < SO₂‐SO > SO₂‐SO₂ i.e. the most oxidized sulfur atoms do not lead to the longest bond lengths. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:346–351, 2005; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20101     

Platinum complexes of dibenzo[1,2]dithiin, dibenzo[1,2]dithiin oxides and related polyaromatic hydrocarbon ligands

The synthesis of platinum bisphosphine complexes of biphenyl- 2,2'-dichalcogenates and the oxides of dibenzo[1,2]dithiin and related ligand systems by oxidative addition to [Pt(PPh(3))(4)] is reported. We also describe the synthesis of a new compound, dibenzothiophen-4-yldiselenide and its simple platinum complex (obtained by oxidative addition). All complexes have been fully characterised, principally by using multinuclear NMR spectroscopy and in six cases by means of single-crystal X-ray diffraction studies. The majority are simple S/S or Se/Se complexes, however the addition of dibenzo[1,2]dithiin trioxide to [Pt(PPh(3))(4)] gives a bimetallic system, [Pt[2-[S(O)],2'-[S(O)(2)]-biphen}(PPh(3))](2), containing a central Pt(2)S(2)O(2) core in which the ligand behaves as a tridentate S,S,O donor.     

Characterization of a Redox-responsive Molecular Switch Based on Dibenzo[1,2]dithiine Using DFT

Structural and electronic properties of a bistable redox-responsive molecular switch based on dibenzo[1,2]dithiine (PSBH) were studied using the DFT-B3LYP/6-31G* method. The results confirmed that the electrical conductivity of the closed form of considered molecular switch is higher than that of the open form. NBO electric charges on heavy atoms of biphenyl unit revealed that the positive charge on sulfur atoms reinforced, which caused the collapse of disulfide bond.     

Synthesis and redox-enzyme modulation by amino-1,4-dihydro-benzo[d][1,2]dithiine derivatives

A convenient method to prepare a series of benzodithiine derivatives was developed, via the synthesis of cyclic disulfide building blocks containing an amino-group linker. Some of the novel cyclic disulfide compounds are shown to modulate the activity of the redox-enzyme glutathione reductase.     

Synthesis of polyoxygenated dibenzo[a,e]cycloheptatrienes

A successive route for the synthesis of substituted dibenzo[a,e]cycloheptatriene 1 was established by the reduction of 2-allylbenzaldehyde 4, the BF₃·OEt₂-mediated intermolecular coupling of 2-allylphenylmethanol 5 with oxygenated benzenes 6, the olefinic oxidative cleavage of 7 and the intramolecular ring-closure of 8. Functionalized anthracene 13 were prepared from 2-vinylbenzaldehyde 9. The key structures were confirmed by X-ray single crystal diffraction analysis.     

Synthesis of new dibenzo[c.e][1,2]oxaphosphorine 2‐oxide containing diols based on diethanolamine

Different approaches were applied to obtain new diol compounds based on dibenzo[c.e][1,2]oxaphosphorine 2‐oxide (DOPO, 1 ) and diethanolamine (DEolA). Of four processes investigated, a four‐step synthesis of 1 containing propionic acid amide of DEolA proved to be the most efficient one. In addition, the intramolecular amine salt of the DOPO derivative with a ring‐opened structure was obtained by reinvestigation of the reaction of DOPO with DEolA and paraformaldehyde. The Atherton–Todd reaction of 1 and DEolA was investigated as well. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 23:146–153, 2012; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.20763     

Quinoneimines and quinonediimines of the dibenzo[ce] [1,2] thiazine 5,5-dioxide series

9(H)-Oxodibenzo[ce][1,2]thiazine 5,5-dioxide and its 9(H)-phenylsulfonylimino-substituted derivative were synthesized. It is shown that the direct bond between the quinoid ring and the substituent attached to nitrogen leads to a decrease in the redox potential of the system and a simultaneous increase in the electrophilic properties of the quinoneimine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1503–1506, November, 1977.     

螺[二苯并[a,j]氧杂蒽-14,9'-芴]的合成及性质

芴酮与2-萘酚在硫酸和3-巯基丙酸的作用下反应得到化合物螺[二苯并[a,j]氧杂蒽-14,9'-芴]. 采用核磁共振、 质谱、 红外光谱和元素分析等对该化合物进行了表征, 并通过X射线衍射法测得了其晶体结构, 确定该化合物是通过二苯并[a,j]氧杂蒽中的含氧六元杂环和芴中的五元环共用一个碳原子形成一个螺环. 利用荧光光谱和热分析等手段对该化合物的性质进行了研究, 结果表明其最大荧光发射峰为366 nm, 熔点为297 ℃, 热分解温度为329 ℃, 具有较高的热稳定性.     

螺[二苯并[a,j]氧杂蒽-14,9’-芴]的合成及性质简

芴酮与2-萘酚在硫酸和3-巯基丙酸的作用下反应得到化合物螺[二苯并[a,j]氧杂蒽-14,9’-芴]. 采用核磁共振、质谱、红外光谱和元素分析等对该化合物进行了表征,并通过X射线衍射法测得了其晶体结构,确定该化合物是通过二苯并[a,j]氧杂蒽中的含氧六元杂环和芴中的五元环共用一个碳原子形成一个螺环. 利用荧光光谱和热分析等手段对该化合物的性质进行了研究,结果表明其最大荧光发射峰为366 nm,熔点为297 ℃,热分解温度为329 ℃,具有较高的热稳定性.     

Synthesis of 2,3,10,11 -tetraalkoxy-substituted tetrahydrobenzo [a] naphtho [1,2-g] quinolizines

2 Four3,10,11-tetraalkoxy-substituted 5,6,15,15a-tetrahydro-8H-benzo[a]naphtho[1,2-g]-quinolizines were prepared by the Pictet-Spengler cyclization of the respective 1-(6,7-dialkoxy-2-naphthylmethyl)-6,7-dialkoxy-1,2,3,4-tetrahydroisoquinolines. The latter compounds were obtained by a chemical reduction of the corresponding dihydro compounds, which, in turn, were formed by a Bischler-Napieralski cyclization of the appropriate amides.     

Synthesis of benzo[1,2]phenaleno[bc]thiophenes

The synthesis of both isomers of benzo[1,2]phenaleno[bc]thiophene namely, benzo[1,2]phenaleno[3,4-bc]-thiophene and benzo[1,2]phenaleno[4,3-bc]thiophene is described.     

Synthesis and electrochemical behavior of a model redox-active thiacalix[4]arene-tetrathiafulvalene assembly

Syntheses of the first bisthiacalix[4]arenes systems bridged by a tetrathiafulvalene (TTF) framework have been carried out through triethyl phosphite-mediated dechalcogenation dimerization of the corresponding 1,3-dithiole-2-ones. The cyclic voltammograms of the resulting bisthiacalix[4]arenes tethered by an electroactive TTF unit are provided, and exhibit an electrochemical response in the case of introduction of Ag⁺.     

Synthesis of Substituted Indolo[1,2- a ]quinoxalines

Abstract

1-(2-Nitrophenyl)indole-2-carboxylates 5, obtained by the N-arylation of indole-2-carboxylates 4, on catalytic reductive cyclization afford indolo[1,2-a]quinoxalino-6(5H)-ones 6. These compounds on reduction with LAH in ether/THF yielded indolo[1,2-a]quinoxalines 7.     

Molecular switch based on a cucurbit[6]uril containing bistable [3]rotaxane

A bistable CB6-based [3]rotaxane with two recognition sites has been prepared very efficiently in a high yield synthesis through CB6 catalyzed 1,3-dipolar cycloaddition; this rotaxane behaves as a reversible molecular switch and exhibits conformational changes caused by the movement of rings under base, acid and heat stimuli from one location to the other.     

Bis(dibenzo[c.e][1,2]oxaphosphorino)dichloroplatinum Complexes

Reaction of a series of P-amino and P-cycloalkoxy dibenzo[c.e][1,2]oxaphosphorines (1), (3) and (5) with cis-bis(benzonitrile)dichloroplatinum(II) afforded the title bis(dibenzooxaphosphorino) complexes (2), (4) and (6), respectively. In the case of chiral P-substituents, the complexes (4) and (6) were obtained in homo and heterochiral forms. Stereospecific ¹J(¹⁹⁵Pt–P) couplings found in the ³¹P-n.m.r. spectra of the products (2), (4) and (6) suggested the cis orientation of the identical substituents.     

One-Pot Synthesis of [1,2]Isoxazolidin-5-ones and [1,2]Oxazin-6-ones

This article has been retracted.