cas 90-94-8, 4,4'-Bis(dimethylamino)benzophenone

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Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions
A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.
Park, Kwihwan,Jiang, Jing,Yamada, Tsuyoshi,Sajiki, Hironao
p. 1200 - 1205
(2021/12/29)

Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis
A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.
Xie, Pan,Xue, Cheng,Du, Dongdong,Shi, SanShan
supporting information
p. 6781 - 6785
(2021/08/20)

One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy
A general one-pot procedure for the 1,2-addition of organolithium reagents to amides followed by the Buchwald-Hartwig amination with in situ released lithium amides is presented. In this work amides are used as masked ketones, revealed by the addition of organolithium reagents which generates a lithium amide, suitable for subsequent Buchwald-Hartwig coupling in the presence of a palladium catalyst. This methodology allows for rapid, efficient and atom economic synthesis of aminoarylketones in good yields.
De Jong, Jorn,Heijnen, Dorus,Helbert, Hugo,Feringa, Ben L.
p. 2908 - 2911
(2019/03/17)

Intramolecular Hydrogen-Bonding Modulates the Nucleophilic Reactivity of Ammonium-Peroxycarboxylates
The ammonium-peroxycarboxylic acid mesylates derived from γ-aminobutyric acid, β-alanine, and β-piperidinopropionic acid were synthesized and characterized by spectroscopic methods and X-ray crystallography. To study the nucleophilic reactivities of the corresponding ammonium- and amino-peroxycarboxylates, the kinetics of their reactions with a series of benzhydrylium ions (Ar2CH+) were investigated in alkaline, aqueous solutions at 20 °C. Using sequential-mixing stopped-flow UV/Vis photometry, the rates of the reactions of the short-lived nucleophiles with Ar2CH+ were determined and analyzed by the linear free energy relationship lg k = sN(N + E) furnishing nucleophilicity parameters (N, sN) of the peroxycarboxylates. Quantum chemical calculations indicate that the reactivity of the zwitterionic ammonium-peroxycarboxylates is attenuated by intramolecular N–H···O hydrogen bonding.
Mayer, Robert J.,Ofial, Armin R.
supporting information
p. 6010 - 6017
(2018/11/10)

A series of BiO: XIy/GO photocatalysts: Synthesis, characterization, activity, and mechanism
A series of bismuth oxyiodide (BiOxIy)-grafted graphene oxide (GO) sheets with different GO contents were synthesized through a simple hydrothermal method. This is the first report where four composites of BiOI/GO, Bi4O5I2/GO, Bi7O9I3/GO, and Bi5O7I/GO have been characterized using X-ray diffraction, transmission electron microscopy, scanning electron microscopy energy-dispersive spectroscopy, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and diffuse reflectance spectroscopy. The assembled BiOxIy/GO composites exhibited excellent photocatalytic activities in the degradation of crystal violet (CV) under visible light irradiation. The order of rate constants was as follows: Bi7O9I3/GO > Bi4O5I2/GO > Bi4O5I2 > Bi7O9I3 > Bi5O7I/GO > BiOI/GO > BiOI > Bi5O7I > GO. The photocatalytic activity of the Bi7O9I3/GO (or Bi4O5I2/GO) composite reached a maximum rate constant of 0.351 (or 0.322) h-1, which was 1.8 (or 1.7) times higher than that of Bi7O9I3 (or Bi4O5I2), 6-7 times higher than that of BiOI/GO, and 119-130 times higher than that of BiOI. The quenching effects of different scavengers and electron paramagnetic resonance demonstrated that the superoxide radical (O2-) played a major role and holes (h+) and hydroxyl radicals (OH) played a minor role as active species in the degradation of crystal violet (CV) and salicylic acid (SA). Possible photodegradation mechanisms are proposed and discussed in this research.
Chou, Shang-Yi,Chung, Wen-Hsin,Chen, Li-Wen,Dai, Yong-Ming,Lin, Wan-Yu,Lin, Jia-Hao,Chen, Chiing-Chang
p. 82743 - 82758
(2016/11/01)

Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water
The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.
Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Yang, Chunlin,Zhu, Xiaoming
supporting information
p. 714 - 718
(2015/03/18)

Imidazo[1,5-a]pyridine-1-ylalkylalcohols: Synthesis via intramolecular cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers and molecular structures
Iodine-mediated cyclization of N-thioacyl 1,2-aminoalcohols derived from aromatic aldehydes and ketones mainly produced bis(1-imidazo[1,5-a]pyridyl) arylmethanes, whereas the reaction of N-thioacyl 1,2-aminoalcohols derived from aliphatic aldehydes and N-thioacyl 1,2-aminoalcohols protected with a silyl group with iodine gave imidazo[1,5-a]pyridine-1-ylalkylalcohols as a major product.
Murai, Toshiaki,Nagaya, Eri,Shibahara, Fumitoshi,Maruyama, Toshifumi
scheme or table
p. 4943 - 4953
(2012/07/28)

(N-Heterocyclic Carbene)-Pd-catalyzed anaerobic oxidation of secondary alcohols and domino oxidation-arylation reactions
The use of commercially available (SIPr)Pd(cinnamyl)Cl (SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene) as a precatalyst for the anaerobic oxidation of secondary alcohols is described. The use of this complex allows for a drastic reduction in the reaction times and catalyst loading when compared to the unsaturated counterpart. This catalytic system is compatible with the use of microwave dielectric heating, decreasing even further catalyst loading and reaction times. Domino Pd-catalyzed oxidation-arylation reactions of secondary alcohols are also presented.(Figure Presented)
Landers, Brant,Berini, Christophe,Wang, Chao,Navarro, Oscar
experimental part
p. 1390 - 1397
(2011/05/02)

Rapid and selective catalytic oxidation of secondary alcohols at room temperature by using (N-Heterocyclic Carbene)-Ni0 systems
The selective, anaerobic catalytic oxidation of secondary alcohols at room temperature by using an in situ (N-heterocyclic carbene)-Ni0 system is presented. The use of non-anhydrous, non-degassed 2,4-dichlorotoluene as both the oxidant and the solvent allows for very short reaction times and very high yields. In addition, a well-defined (N-heterocyclic carbene)-Ni0 complex was synthesized and applied to these oxidation reactions.
Berini, Christophe,Winkelmann, Ole H.,Otten, Jennifer,Vicic, David A.,Navarro, Oscar
supporting information; experimental part
p. 6857 - 6860
(2010/08/03)

Homogeneous, anaerobic (N-heterocyclic carbene)-Pd or -Ni catalyzed oxidation of secondary alcohols at mild temperatures
The use of aryl chlorides as oxidants for the selective oxidation of a variety of secondary alcohols in anaerobic conditions with (NHC)-Pd and -Ni systems (NHC = N-heterocyclic carbene) at very mild temperatures is presented.
Berini, Christophe,Brayton, Daniel F.,Mocka, Corey,Navarro, Oscar
supporting information; experimental part
p. 4244 - 4247
(2009/12/31)

Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine
Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed as the supporting ligand. In each of these cases, commercially available solutions constitute the source of the dimethylamine, and recently disclosed precatalysts constitute the source of the ligand and Pd. This work further expands the utility of these precatalysts in reactions that benefit from an easily activated source of L1Pd(0).
Lee, Brian K.,Biscoe, Mark R.,Buchwald, Stephen L.
supporting information; experimental part
p. 3672 - 3674
(2009/10/04)

Anaerobic palladium-catalyzed chemoselective oxidation of allylic and benzylic alcohols with α-bromo sulfoxide as a Co-oxidant
A chemoselective palladium-catalyzed anaerobic oxidation of allylic and benzylic alcohols using an a-bromo sulfoxide as a co-oxidant is described for the first time. The catalyst system is simple and has a long life because of the allowance of phosphane ligands under the non-aerobic conditions. The advantages of the described method include no overoxidation of primary alcohols to carboxylic acids because of the mild conditions applied, the tolerance of oxygen-sensitive functionalities such as a carbon-carbon double bond, an organothio group, or a diorganoamino group and the effective preparation of α,β-unsaturated aldehydes and ketones, resulting from the oxidation of primary and secondary allylic alcohols, since a competitive Heck reaction with the co-oxidant does not occur.
Rodriguez, Nuria,Medio-Simon, Mercedes,Asensio, Gregorio
p. 987 - 991
(2008/04/03)

An efficient C-C bond cleavage of 1,2-diols using tetraethylammonium superoxide
Tetraethylammonium superoxide, generated in situ by the phase-transfer reaction of potassium superoxide and tetraethylammonium bromide in DMF, brings about an easy cleavage of vicinal diols and related dihydroxy arenes under mild reaction conditions, at room temperature.
Singh, Krishna Nand,Kumar, Rajesh,Shukla, Ajay Kumar
p. 1347 - 1351
(2008/09/18)

Ambident reactivity of the nitrite ion revisited
(Chemical Equation Presented) Lost control: The rationalization of the ambident reactivity of NO2- by the change between charge control to orbital control has to be revised. SN1-type reactions of carbocations with NO2- give kinetically controlled product mixtures only when these reactions proceed without activation energy (diffusion control). Activation-controlled SN1 alkylations are reversible and lead to the thermodynamically more stable nitro compounds.
Tishkov, Alexander A.,Schmidhammer, Uli,Roth, Stefan,Riedle, Eberhard,Mayr, Herbert
p. 4623 - 4626
(2007/10/03)

A novel and selective catalytic oxidation of hydrocarbons to ketones using chloramine-T/O2/Fe(TPP)Cl system
A novel and highly selective oxidation of hydrocarbons to the corresponding ketones using the Fe(TPP)Cl/chloramine-T/O2 system was described.
Li, Shi-Jun,Wang, Yan-Guang
p. 8013 - 8015
(2007/10/03)

Productive chloroarene C-Cl bond activation: Palladium/phosphine-catalyzed methods for oxidation of alcohols and hydrodechlorination of chloroarenes
The palladium/phosphine-catalyzed productive chloroarene C-Cl bond activation provides general, efficient, and functional group friendly methods for the selective oxidation of alcohols and the hydrodechlorination of chloroarenes.
Bei, Xiaohong,Hagemeyer, Alfred,Volpe, Anthony,Saxton, Robert,Turner, Howard,Guram, Anil S.
p. 8626 - 8633
(2007/10/03)

Ytterbium triflate catalyzed Friedel-Crafts reaction: Facile synthesis of diaryl ketones
Friedel-Crafts reaction of aromatic compounds (benzenes, thiophene, furan, pyrrole, naphthalene, and benzothiophene) with bis(trichloromethyl) carbonate [BTC] was efficiently catalyzed by ytterbium triflate [Yb(OTf)3] to give diaryl ketones wit
Su, Weike,Jin, Can
p. 4249 - 4256
(2007/10/03)

Productive utilization of chlorobenzene: Palladium-catalyzed selective oxidation of alcohols
(Matrix presented) The palladium/ligand-catalyzed activation of chlorobenzene provides a general, efficient, and functional group friendly method for the selective oxidation of alcohols to carbonyl compounds.
Guram, Anil S.,Bei, Xiaohong,Turner, Howard W.
p. 2485 - 2487
(2007/10/03)

Selective oxidation of alcohols to aldehydes or ketones
Alcohols are oxidized to their corresponding ketone or aldehyde using an aryl chloride oxidant and a metal-ligand complex or metal/ligand composition. This reaction is particularly applicable to aromatic alcohols and cyclic and bicyclic aliphatic alcohols.
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Example 10

(2008/06/13)

Unusual aminations with tetramethylguanidine
Heating activated halobenzenes with 1,1,3,3-tetramethylguanidine affords mixtures of dimethylaminobenzenes and 2-aryl-1,1,3,3-tetramethylguanidines.
Gabbutt, Christopher D.,Heron, B. Mark,McCreary, Janice M.,Thomas, David A.
p. 69 - 71
(2007/10/03)

Friedel-crafts reaction of BIS(Trichloromethyl)carbonate for the preparation of benzophenones
Benzophenones (RC6H4COC6H4R, R=H, Cl, CH3 or (CH3)2N) have been prepared by the Friedel-Crafts reactions of aromatic compounds C6H5R with bis(trichloromethy
Peng, Xiaojun,Wang, Jingyun,Cui, Jingnan,Zhang, Rong,Yan, Ying
p. 2361 - 2367
(2007/10/03)

Kinetics and Mechanism of the Methyltrioxorhenium-Catalyzed Sulfoxidation of Thioketones and Sulfines
Kinetic studies have been carried out on the oxidation of thiobenzophenones and thiocamphor by hydrogen peroxide and on the second step in the sequence, oxidation of the resulting sulfines (Ar2C= S=O). The first reaction follows the pattern now common to methyltrioxorhenium/H2O2 reactions, in that the rate constant for the reaction between the peroxorhenium intermediate and the thioketone follows a Hammett correlation such that electron-releasing substrates react more rapidly. The reaction constant is p = -1.12. However, the plot of log(kX/kH) for the sulfines against 2σ, determined over the range -1.6 2 under these conditions rather than undergoing disproportionation to SO2 and S. Also, SO was trapped with a 1,3-diene as a thiophene-1-oxide.
Huang, Ruili,Espenson, James H.
p. 6374 - 6376
(2007/10/03)

Effect of BSA binding on photophysical and photochemical properties of triarylmethane dyes
We have employed a combination of steady-state and time-resolved spectroscopic techniques to explore the effect of protein binding on the photophysical and photochemical properties of three triarylmethane dyes: ethyl violet, crystal violet, and malachite green. Our results indicate that the binding sites of bovine serum albumin (BSA) are very efficient in preventing fast nonradiative relaxation processes that occur via rotational motion of the aromatic rings of these triarylmethanes. As a result, remarkable enhancements in fluorescence quantum yield and lifetime, intersystem crossing efficiency, and photoreactivity are observed upon protein binding. The 532 nm laser-induced photobleaching of ethyl violet noncovalently bound to BSA yields leuco ethyl violet and 4,4a?2-bis(diethylamino)benzophenone as reaction products. The former was more prominent in nitrogen-purged samples and the latter in air-equilibrated samples. The time-resolved transient spectra of the ethyl violet complex show superimposed elements of the spectroscopic signatures of both ethyl violet triplet and the semireduced dye radical. Based on the nature of the reaction photoproducts and transient intermediates, the first step of the bleaching process is postulated to be an electron or hydrogen atom transfer from the protein to the dye moiety. An analogous reaction mechanism was observed for protein-bound crystal violet.
Baptista, Mauricio S.,Indig, Guilherme L.
p. 4678 - 4688
(2007/10/03)

Mechanism of dye bleaching upon laser excitation of crystal violet bound to bovine serum albumin
The laser induced photobleaching of crystal violet non-covalently bound to bovine serum albumin yields leuco crystal violet and Michler's ketone as reaction products. The first step of the bleaching process is postulated to be an electron or hydrogen atom transfer from the protein to the dye moiety.
Indig, Guilherme L.
p. 243 - 244
(2007/10/03)

Acetal formation by metal ion-mediated desulfurization-condensation of thioketones with diols and phenols
The acetal formation of thioketones with several diols and phenols through metal ion-mediated desulfurization-condensation was investigated. The reactivities of 4,4′-bis(dimethylamino)thiobenzophenone) "thio-Michler's ketone" (TMK) and xanthene-9-thione (XT) toward α,ω-alkanediols [HO(CH2)nOH, n = 2～4] in the presence of silver trifluoroacetate and triethylamine were compared. The reaction of TMK with glycerol, trans- and cis-1,2-cyclohexanediols, α,α'-dihydroxy-o-xylene and biphenyl-2,2-diol in the presence of silver salt gave the corresponding acetals in good yields. On the other hand, copper(I) chloride, in place of silver(I) salt, was useful for catechol and pyrogallol to give their acetals, respectively. It was thus found that thioketones are new and versatile acetalizing reagents for diols and phenols.
Shibuya, Isao,Katoh, Eisaku,Gama, Yasuo,Oishi, Akihiro,Taguchi, Yoichi,Tsuchiya, Tohru
p. 851 - 859
(2007/10/03)

Reactions of pinacols with one-electron oxidants
Oxidation of the tetraarylpinacols (Ar2COH)2, 1a-e, in which Ar = C6H5 (1a), 4-ClC6H4 (1b), 4-MeC6H4 (1c), 4-MeOC6H4 (1d) and 4-Me2NC6H4 (1e), by thianthrene cation radical (Th?+) in CH3-CN and in CH2Cl2 led quantitatively to the corresponding diaryl ketones Ar2C=O (2a-e), provided a sufficient amount of base, 2,6-di-tert-butyl-4-methylpyridine (DTBMP), was present to prevent presumed acid-catalyzed rearrangement. In the case of 1e, continued oxidation of 2e was also observed. Oxidation of 1a by (4-BrC6H4)3N?+SbCl 6- and (4-BrC6H4)3N?+SbF 6- (Ar3N?+) occurred analogously. Evidence for the catalytic, cation-radical rearrangement of 1a by Ar3N?+ (reported in earlier literature) and by Th?+ could not be found. Quantitative oxidation of 1a to 2a and of 1d to 2d was obtained also with NOBF4, again provided that sufficient DTBMP was present to prevent acid-catalyzed rearrangement. Catalytic, oxidative rearrangement of 1d at room temperature and (as reported in earlier literature) at -5 °C was not observed. Oxidation was also observed of 2,3-diphenyl-2,3-butanediol (3) to acetophenone (9) and of 1,1-dimethyl-2,2-diphenylethanediol (4) to 2a and acetone by Th?+. Oxidation of 2,3-dimethyl-2,3-butanediol (5) by Th?+ was not observed. Instead, even in the presence of DTBMP, pinacolone (10) and tetramethyloxirane (11) were formed, through, it is proposed, a mechanism involving complexation with Th?+.
Han, Dong Sul,Shine, Henry J.
p. 3977 - 3982
(2007/10/03)

TRANSFORMATIONS OF 1,1,1-TRICHLORO-2,2-BIS(4-CHLOROPHENYL)ETHANE, 4,4'-DICHLOROBENZOPHENONE, AND THEIR NITRO DERIVATIVES IN A SODIUM HYDROXIDE-AMIDE SOLVENT MEDIUM
The reaction of 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane with alkali in an amide solvent leads to dehydrochlorination of the substrate.In 1,1,1-trichloro-2,2-bis(3-nitro-4-chlorophenyl)ethane under the same conditions substitution of the chlorine atoms in the bridging group by dimethylamino groups, formed as a result of hydrolysis of the solvent, occurs after dehydrochlorination.In 1,1,1-trichloro-2,2-bis(3,5-dinitro-4-chlorophenyl)ethane the chlorine atoms of benzene ring are substituted by dimethylamino groups.In the presence of CuCl 4,4'-dichlorobenzophenone is converted into 4,4'-bis(dimethylamino)benzophenone. 3,3'-Dinitro-4,4'-dichlorobenzophenone reacts with the sodium hydroxide-amide solvent system with the formation of 3,3'-dinitro-4,4'-bis(dimethylamino)-benzophenone and 3,3'-dinitro-4-hydroxy-4'-dimethylaminobenzophenone, the ratio of which is determined by the reaction temperature.
Sibrikov, S. G.,Kazin, V. N.,Kopeikin, V. V.,Mironov, G. S.,Orlova, T. N.
p. 325 - 327
(2007/10/02)

THIOCARBONYL TO CARBONYL GROUP TRANSFORMATION USING CuCl AND NaOH
A simple and efficient procedure for the rapid and mild conversion of thiocarbonyls to carbonyls is described.
Narasimhamurthy, N.,Samuelson, A. G.
p. 3911 - 3912
(2007/10/02)

REACTIONS OF ORGANOMETALLIC COMPOUNDS, CATALYZED BY TRANSITION METAL COMPLEXES. 8. CARBONYLATION OF ARYLMERCURY COMPOUNDS IN THE PRESENCE OF PALLADIUM AND RHODIUM
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Bumagin, N.A.,Kalinovskii, I.O.,Beletskaya, I.P.
p. 2368 - 2373
(2007/10/02)

OZONIZATION OF TRIPHENYLMETHANE DYES.
The reaction of Malachite Green (MG, 1a), a model compound of triphenylmethane dye, with ozone proceeded via two paths. The first path involved an ozone attack at the dimethylamino moiety to give a N-formylmethylamino derivative. The second path produced 4-(dimethylamino)benzophenone and p-(dimethylamino)phenol. Other ozonized products were also detected. A discussion is presented of the ozonization mechanism.
Matsui,Nakabayashi,Shibata,Takase
p. 3312 - 3316
(2007/10/02)

THE REACTION OF t-BUTYL HYPOCHLORITE WITH THIOCARBONYL COMPOUND - A CONVENIENT METHOD FOR THE TRANSFORMATION
The reaction of t-butyl hypochlorite with different thiocarbonyl compounds has been studied.Primary thioamides 1a-c give 1,2,4-thiadiazole derivatives.N-Phenylthiourea 4a gives 5-imino-4-phenyl-3-phenylamino-4,5-dihydro-1,2,4-thiadiazoline 15.Secondary and tertiary thioamides 2a-d, N-methyl-2-thiopyrrolidinone 3, N,N'-dicyclohexylthiourea 4b, N,N,N'-trimethylthiourea 4c, 5-ethyl-5-phenylthiobarbituric acid 5, xanthione 7a, Mischler's thioketone 7b, thiocoumarin 8, O-ethylthiobenzoate 9, O,O-diphenylthiocarbonate 10, di-p-tolyl and o-phenylene trithiocarbonates 11 and 12 have all afforded the oxigen analogues.N,N-Dimethyl-S-phenyldithiocarbonate 6 produces a mixture of di-, tri-, and tetrasulfides.A mechanism for the transformation is suggested in accordance with the Hard and Soft Acids and Bases (HSAB) principle.
El-Wassimy, M.T.M.,Jorgensen, K.A.,Lawesson, S.-O.
p. 1729 - 1734
(2007/10/02)

THE =C=S -> =C=O TRANSFORMATION USING THE SOFT NO(+)-SPECIES
The reaction of NaNO2 in acidic solution with thiocarbonyl compounds has been studied.Secondary- and tertiary thioamides, 1-benzyl-hexahydro-2H-azepine-2-thione, 5-ethyl-5-phenyl thiobarbituric acid, certain thiourea derivatives, 2H-1-benzopyran-2-thione, O,O-diphenyl-thiocarbonic ester, O,S-diphenyl-dithiocarbonic ester, N,N-dimethyl-S-phenyl-dithiocarbamatic ester, N-ethyl-N-phenyl-O-ethyl-thiocarbamatic ester are all converted into the corresponding carbonyl-analogues. 4,4'-Bis(dimethylamino)-thiobenzophenone (Michler's thioketone) gives 3-nitro-4,4'-bis(dimethylamino)-benzophenone at room temperature.At (-10 deg C)-(-5 deg C) the expected oxo compound is obtained as the main product together with 4-(N-nitroso-methylamino)-4'-(dimethylamino)-benzophenone.
Joergensen, K. A.,Ghattas, A.-B.A.G.,Lawesson, S.-O.
p. 1163 - 1168
(2007/10/02)