6637-60-1Relevant academic research and scientific papers
Syntheses of acyclic C-glycosidic derivatives of 1,2,4-triazoles by cycloadditions of 1-aza-2-azoniaallene salts to D-glucononitrile- 2,3,4,5,6-pentaacetate
Hassan
, p. 933 - 936 (2007)
(Chemical Equation Presented) Reported are preparations of acyclic derivatives of 1,2,4-triazole-5-glycosidies 9 by cycloadditions of 1-aza-2-azonia-allene salts 3 to the nitrile group of D-glucononitrile-2,3,4,5, 6-pentaacetate 5 affording triazolium sal
Dialkoxymethano[60]fullerenes as electron acceptors in thin-film organic solar cells
Suleiman, Mohammed Y.,Ma, Yue,Nakagawa, Takafumi,Ueno, Hiroshi,Matsuo, Yutaka
, (2019)
This study presents the synthesis, characterization, and electrochemical properties of four new dialkoxymethanofullerenes, as well as their performance in organic solar cells (OSCs) devices. Dialkoxymethanofullerenes were synthesized in 27%–32% yield by thermolysis of dialkoxyoxadiazolines and reaction with C60 under reflux in toluene. The prepared compounds were then characterized and used for the first time as electron-acceptor materials in thin-film bulk heterojunction OSCs with PBTZT-stat-BDTT-8 as the electron donor material. The devices made with ethoxy-hexyloxymethanofullerene and methoxy-hexyloxymethanofullerene exhibited optimal power conversion efficiencies (PCEs) of 3.79% and 4.65%, with open-circuit voltage of 0.832 and 0.831 V, respectively. In contrast, the devices made with ethoxy-ethoxymethanofullerene and methoxy-ethoxymethanofullerene exhibited very low PCEs of 0.01% for both, indicating a large impact of the substituents on device performance.
CuI-catalyzed cross-coupling of terminal alkynes with dialkoxycarbenes: A general method for the synthesis of unsymmetrical propargylic acetals
Xiao, Tiebo,Zhang, Ping,Xie, Yang,Wang, Jun,Zhou, Lei
, p. 6215 - 6222 (2014/08/05)
A general source of dialkoxycarbenes, 2,2-dialkoxy-5,5-dimethyl- Δ3-1,3,4-oxadiazolines, have been successfully employed as coupling partners in CuI-catalyzed cross-coupling reactions with terminal alkynes, which afforded various unsymmetrical propargylic acetals in good yields. This journal is the Partner Organisations 2014.
Synthesis of lithium 1-alkynesulfenates by the mild oxidation of thiolates with a pinacolone-derived N-sulfonyloxaziridine
Sandrinelli, Franck,Boudou, Cédric,Caupène, Caroline,Averbuch-Pouchot, Marie-Thérèse,Perrio, Stéphane,Metzner, Patrick
, p. 3289 - 3293 (2008/09/18)
Lithium 1-alkynethiolates, generated by a base-induced ring cleavage of 4-substituted 1,2,3-thiadiazoles, were efficiently converted into the corresponding sulfenate salts by mild oxidation using an N-sulfonyloxaziridine derived from pinacolone. In situ S
The α-effect in iminium ion catalysis
Cavill, Julie L.,Elliott, Richard L.,Evans, Gareth,Jones, Ian L.,Platts, James A.,Ruda, Antonio M.,Tomkinson, Nicholas C. O.
, p. 410 - 421 (2007/10/03)
The α-effect can be used as an effective means to promote iminium ion catalysed transformations, providing acyclic scaffolds to aid in catalyst design. A thorough investigation of the structure-activity relationship of the catalyst architecture reveals optimal substituents of a disubstituted carbamate and a secondary alkyl group around a hydrazine scaffold. Molecular modelling investigations provide a mechanistic rationale to the results observed.
Iminium ion catalysis: Use of the α-effect in the acceleration of the Diels-Alder reaction
Cavill, Julie L.,Peters, Jens-Uwe,Tomkinson, Nicholas C. O.
, p. 728 - 729 (2007/10/03)
The α-effect can be used in the acceleration of the DielsAlder reaction between a series of dienes and electron deficient dienophiles using iminium ion catalysis, providing a novel molecular scaffold capable of performing this class of catalytic process.
The synthesis of azapeptidomimetic beta-lactam molecules as potential protease inhibitors.
Malachowski, William P,Tie, Chenyang,Wang, Katherine,Broadrup, Robert L
, p. 8962 - 8969 (2007/10/03)
Synthetic methods for the construction of a novel peptidomimetic structure are reported. The structure incorporates a beta-lactam and an azapeptide in a peptide backbone with the intention of generating rationally designed substrate-based protease inhibitors. The beta-lactam is formed by subjecting serine or threonine-azapeptides to Mitsunobu reaction conditions. Importantly, the azapeptidomimetic beta-lactam structure permits extended binding inhibition and the synthetic methods to create tetrapeptidomimetic structures are described.
Syntheses of C- and N-nucleosides from 1-aza-2-azoniaallene and 1,3-diaza-2-azoniaallene salts
Al-Masoudi, Najim,Hassan, Nasser A.,Al-Soud, Yaseen A.,Schmidt, Patrick,Gaafar, Alaa El-Din M.,Weng, Min,Marino, Stefano,Schoch, Annette,Amer, Atef,Jochims, Johannes C.
, p. 947 - 953 (2007/10/03)
C-Nucleosides are prepared by cycloaddition of 1-aza-2-azoniaallene salts 2 and 1,3-diaza-2-azoniaallene salts 5 to the triple bonds of a glycosylalkyne and of glycosyl cyanides. Thus, the glucosylalkyne 7 reacts with salts 5 to give the 4-glucosyl-1,2,3-
Intramolecular 1,2-alkyl shifts in unsymmetric dialkoxycarbenes studied by very low vapour pressure (VLVP) pyrolysis - mass spectrometry
Suh,Pole,Warkentin,Terlouw
, p. 544 - 548 (2007/10/03)
Methoxy-(2,2,2-trifluoroethoxy)carbene radical cations, CH3O-C-OCH2CF3·+, 1·+, are cleanly generated by the dissociative electron ionization (EI) of 2-methoxy-5,5-dimethyl-2-(2, 2,2-trifluoroethoxy)-Δ3-1,3,4-oxadiazoline I. Neutralization-reionization (NR) mass spectrometry of the neutral carbene 1, generated by one-electron reduction of 1·+, shows no recovery ion signal and thus 1 is not a viable species within the μs time scale of the experiment. Very low vapour pressure (VLVP) pyrolysis - mass spectrometry of I in conjunction with (multiple) collision experiments shows that 1 completely isomerizes, via a 1,2-trifluoroethyl shift, into methyl 3,3,3-trifluoropropionate, CF3CH2C(=O)OCH3, 1a. This technique was also used to study the related dialkoxycarbenes C2H5O-C-OCH2CF3, 2, CH3O-C-OC2H5, 3, and CH3O-C-OCH(CH3)2, 4, generated from the corresponding 2,2-dialkoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazolines. The pyrolytically generated carbene 2 behaves analogously to 1 and completely isomerizes to ethyl 3,3,3-trifluoropropionate, 2a. The neutral carbenes 3 and 4 undergo only a partial isomerization via 1,2-alkyl shifts in which the ethyl and isopropyl groups show a slightly greater migratory aptitude, respectively, than the methyl group. The differences in migratory aptitude are explained in terms of a transition state model similar to that of a 1,2-H shift in carbenes, with development of negative charge in the migrating group. The greater migratory aptitude of CF3CH2, as compared to CH3 and CH3CH2, is attributed to the stabilization of negative charge in the transition state by strongly electron-withdrawing β-fluorines whereas the differences in migratory aptitude between the alkyl groups in 3 and 4 are largely due to the greater polarizability of isopropyl and ethyl groups, as compared to the methyl group.
On triazoles. XXXIV. The correct structure of the ethoxycarboxylated 5-amino-1H-1,2,4-triazole and its product with hydrazine
Reiter
, p. 745 - 748 (2007/10/02)
The structure of the ethoxycarboxylated product of 5-amino-1H-1,2,4-triazole and its hydrazide was corrected using their ir, pmr, cmr and mass spectra.
