42467-40-3

Upstream product

• 591-09-3 nitro acetate 
• 588-59-0 stilbene 
• 4914-12-9 diethyl 2-nitrobenzylphosphonate 
• 3284-77-3 1-(dichloromethyl)-2-nitrobenzene 
• 24974-75-2 2-nitrobenzylsulfonyl chloride 
• 612-23-7 2-nitrobenzyl chloride 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 42546-50-9 (2-nitrobenzylidene)triphenylphosphorane 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 6275-02-1 1,2-bis(o-nitrophenyl)ethylene 
• 23308-83-0 (2-nitrobenzyl)triphenylphosphonium bromide 
• 552-89-6 2-nitro-benzaldehyde 
• 25407-11-8 1,2-bis(2-nitrophenyl)ethyne 
• 88-72-2 1-methyl-2-nitrobenzene 

Downstream Products

• 552-16-9 ortho-nitrobenzoic acid 
• 552-89-6 2-nitro-benzaldehyde 
• 617-20-9 2,2'-diaminostilbene 
• 69395-24-0 2'-nitro-stilben-2-ylamine 
• 32566-01-1 2-(2-aminophenyl)-1H-indole 
• 28096-87-9 2,2'-diaminostilbene 
• 65610-75-5 indolo[1,2-c]quinazolin-6(5H)-one 
• 18735-98-3 5,11-dihydro-indolo[3,2-c]quinolin-6-one 
• 499982-87-5 4-cholesten-3-one (1R,2R)-1,2-bis(2-nitrophenyl)ethane-1,2-diol ketal 
• 178265-14-0 (E)-2,2'-diazidostilbene 

Relevant academic research and scientific papers

Influence of Steric Effects on the Excited Triplet-State Lifetime of 2,2'-Dinitrostilbene and 2,2',4,4',6,6'-Hexanitrostilbene in Acetonitrile Solution

Solutions of 4,4'-dinitrostilbene, 2,2'-dinitrostilbene, 2,2',4,4',6,6'-hexanitrostilbene (HNS), and deuterated derivatives of HNS in acetonitrile have been studied by laser flash photolysis.Transient species with decay lifetimes of 125, 55, and 21 ns, respectively, were observed for the nondeuterated compounds.The decay lifetimes for these species provide evidence that the excited triplet-state lifetime is being reduced as steric hindrance to molecular planarity is increased.This is partly attributed to a reduction in the S0-T1 energy gap of the perpendicular configuration with increasing intramolecular steric hindrance although, for HNS, rapid formation of photoproducts also occurs.The degree of intramolecular steric hindrance associated with nitro groups ortho to the central double bond is indicated by singlet ground-state absorption measurements.

Non-conventional synthesis and photophysical studies of platinum(ii) complexes with methylene bridged 2,2′-dipyridylamine derivatives

Methylene bridged 2,2′-dipyridylamine (dpa) derivatives and their metal complexes possess outstanding properties due to their inherent structural flexibility. Synthesis of such complexes typically involves derivatization of dpa followed by coordination on metals, and may not always be very efficient. In this work, an alternative synthetic approach, involving the derivatization step after-rather than prior to-coordination of dpa on metal center, is proposed and applied to synthesis of a number of platinum(ii) complexes with substituted benzyldi(2-pyridyl)amines. Comparison with the more conventional synthetic route reveals greater efficiency and versatility of the proposed approach. The obtained complexes are not luminescent in solution at room temperature, but display blue phosphorescence emission (ca. 415 nm) with the lifetimes of μs order in glassy matrix at 77 K, with additional green (ca. 485 nm) and relatively long living (τ = 3.7 ms) emission in the case of iodine substituted derivative.

Synthesis of stilbene analogues by one-pot oxidation-Wittig and oxidation-Wittig-Heck reaction

Synthesis of symmetrical (and unsymmetrical) stilbene derivatives is achieved by a combination of one-pot steps of Kornblum type oxidation of benzyl halide, its simultaneous in situ formation of phosphonium salt, and subsequently their Wittig reaction. In other variant it is oxidized to aldehyde, treated with ylide generated from phosphonium salt (CH3PPh3X) to give styrene, and subjected to Pd catalyzed Heck reaction with arylhalide to give stilbenes as the three-step one-pot sequence.

Bis(o-nitrophenyl)ethanediol: A practical photolabile protecting group for ketones and aldehydes

The ketals of bis(o-nitrophenyl)ethanediol and ketones or aldehydes are smoothly deprotected in neutral conditions by irradiation with 350 nm light. The chemical stability in basic, acidic, and oxidizing media makes this form of protection orthogonal to classical protecting groups. Both racemic and enantiopure forms are readily available in two steps from inexpensive starting materials.

Selective homogeneous palladium(0)-catalyzed hydrogenation of alkynes to (Z)-alkenes

Zero-valent palladium precatalysts containing rigid bidentate bis(arylimino)acenaphthene ligands (shown schematically) facilitate the highly stereoselective homogeneous catalytic hydrogenation of alkynes to (Z)- alkenes. Internal, terminal, aryl-substituted, and cyclic alkynes are suitable substrates, as are some enynes, which are chemoselectively hydrogenated to dienes. E=CO2Me; R1, R2 = 4-OCH3, 4-CH3, 2,6-(CH3)2.

trans-2,2′-dinitrostilbene as a precursor of 0-nitrobenzaldehyde, a key intermediate for pharmaceuticals: Reactivity and molecular structure studies

A novel synthesis of o-nitrobenzaldehyde by means of the ozonolysis-reductive hydrolysis of symmetrical trans-2,2′-dinitrostilbene is reported, yielding only the ortho isomer of nitrobenzaldehyde. This new route reduces environmental hazards in the synthesis of o-mtrobenzaldehyde. The central ethylene bond of trans-2,2′-dinitrostilbene showed a high reactivity for the ozonolysis reaction. The molecular structures of 2-nitrobenzaldehyde and trans-2,2′-dinitrostilbene were studied theoretically by means of ab initio quantum mechanical calculations at the 6-31G*//6-31G* level. A non-coplanar conformer was found for o-nitrobenzaldehyde, where the carbonyl and nitro groups are slightly twisted with respect to the phenyl ring. Also, a non-coplanar minimal s-trans-gauchels-transgauche conformer (NO2-aryl-C=C-aryl-NO2) was found for trans-2,2′-dinitrostilbene, where the aromatic groups are twisted with respect to the central double bond, and the nitro groups are also twisted out the planes of the aromatic rings. This structure is consistent with certain experimental physical-chemical properties of this molecule.

New models for the study of the racemization mechanism of carbodiimides. Synthesis and structure (X-ray crystallography and 1H NMR) of cyclic carbodiimides

The crystal and molecular structure of carbodiimides 2 (5,6,18,19-tetradehydro-5,12,13,18,25,26-hexahydrotetrabenzo[d,h,m,q][1,3,10,12] tetraazacyclooctadecine) and 3 (8,10,22,24-tetraazapentacyclo-[23.3.1.3,7.111,15.1 17,21]dotriaconta-1(29),3,5,7(32),8,9,11,13,15(31),17,19,21(30),22, 23,25,27-hexadecaene) have been determined. The activation barriers for the racemization of carbodiimides 1 (6,7-dihydrodibenzo[d,h][1,3]diazonine), 2, and 3 have been determined. While 1 presents a relatively high barrier (17.4 kcal mol-1), 2 and 3 have very low activation barriers (between 5 and 7 kcal mol-1). We tentatively conclude that open-chain and large-ring carbodiimides racemize by nitrogen inversion or trans-rotation while medium-size cyclic carbodiimides racemize by cis-rotation.

Reaction of N-fluoropyridinium salts with Wittig reagents: A novel and convenient approach to symmetric trans-olefins

N-Fluoropyridinium salts were found to react with Wittig reagents containing electron-withdrawing groups to give olefins in 47-83% yield. The mechanism of this conversion is believed in involve single-electron transfer from Wittig reagent to N-fluoropyridinium cation.

Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines. 2. Formation of Episulfones, Sulfonylsulfene - Amine S,N-Adducts and Chlorsulfines from Primary Sulfonyl Chlorides and Tertiary Amines

The reaction of primary sulfonyl chlorides 1b-m with the tertiary amine bases quinuclidine, DABCO, Me3N, Et3N, Bu3N, EtiPr2N, and 1,2,2,6,6-pentamethylpiperidine is studied in acetonitrile solution between -40 and 80 deg C.The 2,3-dialkylthiirane 1,1-dioxides 4 (trans/cis > 1) and the alkenes 5 1> are obtained in high yields with Et3N at -40 deg C.The stereochemistry is influenced by the amine base B in the ring-closure reaction and partially by epimerization of the episulfones 4.Hindered bases favor the cis, β-branched sulfonyl chlorides the trans isomer.Competing formation of the sulfonylsulfene - amine S,N-adducts 7 is only observed with quinuclidine, DABCO, and Me3N, which are also the most active amines in the epimerization of the cis-2,3-diarylthiirane 1,1-dioxides 4.Methanesulfonyl chloride (1a) yields the mesylsulfene - amine S,N-adducts 7a with Me3N and Et3N in MeCN, but thiirane 1,1-dioxide (4a) with EtiPr2N in MeCN or with Et3N in Et2O.Formation of chlorosulfines 10 is favored by higher temperature (T > 20 deg C), hindered amine bases and β-branched sulfonyl chlorides.Isolation of 10g and 10h in high yields shows that tert-alkylchlorosulfines are rather stable sulfines.

Reductive Coupling of Geminal Dichlorides by Iron(II) Oxalate Dihydrate

A facile procedure for the quantitative conversion of geminal dichlorides to E olefins with iron(II) oxalate dihydrate in refluxing anhydrous dimethylformamide under a nitrogen atmosphere is described.The coupling proceeds via the corresponding vicinal dichlorides.