19357-64-3Relevant academic research and scientific papers
High-Intensity Laser-Jet Photochemistry: Formation of Benzocyclobutenedione from 1,2,3-Indantrione via Transient Targeting
Adam, Waldemar,Patterson, Wesley S.
, p. 7769 - 7773 (1995)
The photochemistry of 1,2,3-indantrione (1) under high-intensity (laser-jet) conditions has been investigated.Irradiation of trione 1 in a benzene solution under laser-jet conditions produces a complex mixture in which benzocyclobutenedione (2) is observed to be the sole high-intensity product (ca. 11percent yield, six cycles, 3..5 W MLUV argon ion laser) as compared to conventional irradiation (dispersed laser beam, 20 min, 3.5 W MLUV argon ion laser).Under similar conditions, dione 2 was not observed to undergo photolysis in the laser-jet (mass balance ca. 90percent).Additionally, phthalic anhydride, (E)-1,1'-bis-isobenzofuranylidene-3,3'-dione ((E)-4), and 2-benzopyrano-benzopyran-6,12-dione (5) were identified also in both the laser-jet and conventional irradiations of both trione 1 and dione 2.In view of the previously reported product studies, it is proposed that the formation of dione 2 under laser-jet conditions occurs by a photochemical electrocyclization of the intermediary cyclohexadiene-1,2-bisketene (B).The decarbonylation of trione 1 to bisketene B and the electrocyclization of the transient bisketene B to dione 2 constitute an unprecedented sequential multiple-photon transformation of polyketones in solution, which has been uncovered through product studies by using the novel laser-jet technique.
Palladium-Catalyzed Double Carbonylative Cyclization of Benzoins: Synthesis and Photoluminescence of Bis-Ester-Bridged Stilbenes
Tani, Yosuke,Ogawa, Takuji
, p. 7442 - 7446 (2018)
A palladium-catalyzed double carbonylative cyclization of benzoins has been developed, which realizes the synthesis of bis-ester-bridged stilbenes just in two steps from aldehydes. Thus, the obtained fully fused tetracyclic π-systems have a pyrano[3,2-b]pyran-2,6-dione (PPD) core on their center, showing two reversible reductions at low potentials. In addition, their photoluminescence properties are strikingly affected by the aromatic rings fused to the PPD core; bis-thieno-fused PPDs are found to be excellent fluorophores with quantum yields up to 0.98.
Multiple-State Emissions from Neat, Single-Component Molecular Solids: Suppression of Kasha's Rule
Chen, Bin,Chen, Yu-Zhe,Tung, Chen-Ho,Weiss, Richard G.,Wu, Li-Zhu,Wu, Ya-Hang,Xiao, Hongyan
supporting information, p. 10173 - 10178 (2020/03/13)
Three rigid and structurally simple heterocyclic stilbene derivatives, (E)-3H,3′H-[1,1′-biisobenzofuranylidene]-3,3′-dione, (E)-3-(3-oxobenzo[c] thiophen-1(3H)-ylidene)isobenzofuran-1(3H)-one, and (E)-3H,3′H-[1,1′-bibenzo[c] thiophenylidene]-3,3′-dione, are found to fluoresce in their neat solid phases, from upper (S2) and lowest (S1) singlet excited states, even at room temperature in air. Photophysical studies, single-crystal structures, and theoretical calculations indicate that large energy gaps between S2 and S1 states (T2 and T1 states) as well as an abundance of intra and intermolecular hydrogen bonds suppress internal conversions of the upper excited states in the solids and make possible the fluorescence from S2 excited states (phosphorescence from T2 excited states). These results, including unprecedented fluorescence quantum yields (2.3–9.6 %) from the S2 states in the neat solids, establish a unique molecular skeleton for achieving multi-colored emissions from upper excited states by “suppressing” Kasha's rule.
New coupling reactions of some acyl chlorides with samarium diiodide in the presence of samarium: Carbinols from three acyl units
Clausen, Christian,Weidner, Ingo,Butenschoen, Holger
, p. 3799 - 3806 (2007/10/03)
A mixture of samarium(II) iodide and samarium can induce a coupling reaction of three molecules of alkanoyl halide to give trialkylcarbinols of 2-hydroxy-1,3-diones. When aliphatic, unbranched alkanoyl chlorides are used, this new coupling reaction provides trimeric products as the main reaction products. Tetrahydropyran (THP) proved superior as the solvent because no ring-opening and subsequent reaction with the alkanoyl halides was observed under the reaction conditions, unlike when THF was used. Wiley-VCH Verlag GmbH, 2000.
ELECTROCHEMICAL REDUCTION OF PHTHALYL CHLORIDE. A NEW ROUTE FOR THE SYNTHESIS OF 3-SUBSTITUTED PHTHALIDES
Guirado, Antonio,Barba, Fructuoso,Hursthouse, Michael B.,Martinez, Antonio,Arcas, Aurelia
, p. 4063 - 4066 (2007/10/02)
The cathodic reduction, under various conditions, of phthalyl chloride enables efficient synthesis of (E)-biisobenzofuranyliden-3,3'-dion(4), (2)-benzopyrano - benzopyrano-6,12-dione (7), 3-chlorophtalide (8), phtalide (9), or (E)-3 phtalide (12); the structure of the latter compound was confirmed by X-ray crystallography.
Photochemical and Thermal Transformations of Unsymmetrical Di-O-alkyl-S,S-phthaloyl Dixanthates
Darji, R. R.,Shah, A.
, p. 509 - 511 (2007/10/02)
Phthaloyl chloride (I) reacts with potassium O-alkylxanthates at 0 deg C in ether to give the corresponding unsymmetrical di-O-alkyl-S,S-phthaloyl dixanthates (V).Irradiation of these dixanthates (V) in benzene with a mercury lamp for 7 hr results in the formation of trans-biphthalyl (X).However, thermal decomposition of the dixanthates Va (R = isopropyl) and Vc (R = isoamyl) around 250 deg C for 30 min yields a mixture of X, thiophthalic anhydride (XII), carbonyl sulphide (XIV) and the corresponding O,S-dialkyl xanthates (XIII).
Studies on the Occurence of Hydrogen Transfer, 67. Enediol Diesters by Acylating Electroreductive Dimerization of Acyl Chlorides with Lithium Amalgam
Horner, Leopold,Dickerhof, Karlheinz
, p. 1603 - 1614 (2007/10/02)
Aromatic, aliphatic, and aromatic-aliphatic acyl chlorides (and anhydrides) are transformed by lithium amalgam (Li/Hg) to cis- and/or trans enediol diesters 1-10 (acylating reductive dimerization), mostly in ca. 70percent yields.The influence of the solvent on the reaction course is investigated.Starting from 2,2'-biphenyldicarbonyl dichloride, the phenanthrene 7 is formed; phthalide 8 is the reaction-product using phthaloyl dichloride as starting material.Diphenylphosphinyl chloride is reduced by Li/Hg to tetraphenyldiphosphane dioxide (15).A reaction mechanism for the acylating reductive dimerization is proposed on the basis of the halve-wave potentials determined for 12 acyl chlorides and four 1,2-diketones.The latter are intermediates in the acylating reductive dimerization of the acyl chlorides.Enediol diesters are obtained starting from 1,2-diketones and Li/Hg in the presence of acyl chlorides.Trimethylsilyl chloride is unsuitable as a trap for the enediols; it is preferentially reduced at the Li/Hg interface.Tetrahydrofuran as solvent is transformed to RC(O)O-4-Cl by a known ring-opening acylation reaction in the presence of Lewis acids (LiCl or ZnCl2) formed by the decomposition of Li/Hg and Zn/Hg.
A NEW SYNTHESIS OF TRANS-BIPHTHALYL
Guirado, A.,Barba, F.,Martin, J.
, p. 327 - 330 (2007/10/02)
Sym-phthaloyl chloride under controlled cathodic reduction is converted into trans-: trans-biphthalyl in 65percent yield.
New Olefin and Oxiran Syntheses from Carbonyl Compounds, and Diethyl Sodiophosphonate Anions and 1-Aminophosphonate Amino-anions
Minami, Toru,Matsuzaki, Narihide,Ohshiro, Yoshiki,Agawa, Toshio
, p. 1731 - 1738 (2007/10/02)
Reaction of aromatic aldehydes, and phthalic and thiophthalic anhydrides, with diethyl sodiophosphonate (1) gives the trans-stilbenes (3), 3,3'-biphthalidylidene (30), and 3,3'-bis-(2-thiophthalidylidene) (33).Similar treatment of fluorenone (8) and xanthone (17) with (1) leads to 9,9'-bis(fluororenylidene) (9) and 9,10-dihydro-9-oxophenanthrene-10-spiro-9'-fluorene (10), and to 9,9'-bixanthenylidene (18) and 9,9'-bixanthenyl (19), respectively, but the reaction using anthrone (11) as a carbonyl reagent yields only anthraquinone (12) and anthracene (13).Similar treatment using N-methylisatoic anhydride (34) and N-methylisatin (36) produces NN'-dimethylisoindigo (35).Reaction of benzaldehyde and p-chlorobenzaldehyde with diethyl 1--cyclohexylphosphonate (40) gives mainly corresponding mixtures of trans- (41a,b) and cis-stilbene epoxides (42a,b), while similar treatment of p-nitrobenzaldehyde with (40) produces 4,4'-dinitrostilbene (3e).Reaction of (8) with (40), as well as with (1), gives (9) and (10).The mechanism of formation of these products is discussed.
