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1.
采用3-(4-三氟甲基苯亚甲基)吲哚啉-2-酮和2-(4-三氟甲基苯亚甲基)-1H-茚-1,3(2H)-二酮分别与鉮盐在二氯甲烷中,碳酸钾或氟化钾存在下反应,可高产率、高立体选择性地得到以反式构型为主的含三氟甲基的3'-螺环丙基取代的氧化吲哚和2'-螺环丙基取代的茚二酮衍生物.产物相对构型经X射线单晶衍射或1H-1H NOESY谱确定.还从反应机理的角度对产物构型做了解释. 相似文献
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Villemin[1]曾报道KSF/蒙托土催化下微波促进1-苯基-3-甲基-5-吡唑啉酮(1)与醛2的缩合反应,李晓陆[2研究了该反应的固相缩合,Sun[3]报道了KF-Al2O3催化下甲醇溶液中的反应.本文采用绿色合成原则,无催化剂条件下无溶剂微波辐射及水中回流方法研究了此反应,得到两类化合物(图1).产物结构经1H NMR,13C NMR,MS及IR确证.实验发现辐射功率对产物有很大影响,高辐射功率下得到4-芳甲叉-3-甲基-1-苯基-5-吡唑啉酮(3),低辐射功率得到4,4′-芳甲叉-双(3-甲基-1-苯基-5-吡唑啉酮)(4);水相反应同时得到两种产物,以产物3为主(表1).产物结构与反应物配比无关. 相似文献
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Habrant D Stengel B Meunier S Mioskowski C 《Chemistry (Weinheim an der Bergstrasse, Germany)》2007,13(19):5433-5440
A study of the reactivity of semi-stabilised arsonium ylide anions in olefination reactions is presented. The different ylide anions were generated by the addition of nBuLi to various arsonium halide derivatives: [Ph(2)As(R)R'](+)X(-), where R and R' are methyl, allyl, prenyl or benzyl groups. By using diallyldiphenylarsonium bromide (R=R'=allyl) an olefination protocol was optimised allowing the efficient transformation of aliphatic aldehydes into terminal 1,3-dienes with a high selectivity for the E isomer (E/Z ratios ranging from 90:10 to 97:3). The olefination reactions of aldehydes with dissymmetric arsonium halides (R not equal R') are very chemoselective; with arsonium ylide anions the benzyl moiety is more reactive than the allyl moiety which is much more reactive than prenyl and methyl groups. Based on the experimental results, a mechanism is proposed for the reaction. 相似文献
12.
The crystals of pentafluoropropionylbenzoylmethylene triphenylphosphorane that bears two strongly electron-withdrawing groups in alkylidene moiety are monoclinic and its space group is C2/c, with a = 11.271(3)Å, b = 18.253(6)Å, c =23.938(7)Å, β = 91.09(2)°, z = 8. The X-ray diffraction intensity data were collected on a four-circle diffractometer. The structure has been solved by direct method and refined by block-diagonal least-squares method. The final R- index was 0.075 for 3146 independent observed reflexions. In this paper the structure of this ylide is compared with that of corresponding arsonium ylide previously reported. Both ylidic skeleton structures are planar with sp2 hybridization. The bond length of P-C(1) is 1.748 (5)Å with bond order. 1.60 while the bond order of As-C(1) in the corresponding arsonium ylide is 1.46, indicating that the phosphonium ylide has a greater contribution of “ylene” structure to the overall structure. As a result the phosphonium ylide should be less reactive than the corresponding arsonium ylide. In both ylides, (he major delocalized canonical forms of negative charge are shown to be 3. 相似文献
13.
As the first example 4 of the Wittig reaction of α-halo substituted semistabilized arsonium ylide, we utilized this reaction to synthesize vinyl iodides 5. 相似文献
14.
(p-Nitrobenzylidene)triphenylarsenane, a semistabilized arsonium ylide has been prepared and reacted with carbonyl compounds to yield olefins as opposed to epoxidation products. Treatment of the ylide with a ranged acyl halides gave new disubstituted arsonium ylides. IR and NMR spectral data for the resulting products are reported. 相似文献
15.
D. A. Chuvashov I. V. Vakulin F. Z. Galin R. F. Talipov 《Theoretical chemistry accounts》2007,118(2):363-369
The effect of temperature and keto ylides structure on preference of their intramolecular cyclization leading to N-containing
heterocyclic compounds or linear products formation has been investigated at the B3LYP/6-31G(d,p) level of theory. It has
been determined that the thermodynamic advantage of the cyclization reactions of ylides increases with temperature, while
Gibbs free energies of linear products formation reactions depend insignificantly on temperature. The Wittig and the Corey–Chaykovsky
reactions are least probable in the case of the sulfonium and ammonium ylides considered. However, for phosphonium ylides
the Wittig reaction must be considerably preferable in comparison with other routes, while behavior of the arsonium ylides
is predicted to be more complex. Research of S-ylides transformations shows that formation of methylthio-substituted heterocycles
with five-, six- or seven- membered rings is possible from a thermodynamic standpoint, while conversion of the corresponding
ylide to a four-membered heterocycle is disadvantageous. Presence of a methyl substituent and its position in the ylide carbon
chain depends ambiguously on the behavior of sulfur keto ylides. 相似文献
16.
Allylic sulfonium salts 3, 5, 7, 11, 12, 13, and arsonium salt 14 react with aromatic, heteroaromatic, and alpha,beta-unsaturated N-sulfonylimines under solid-liquid phase-transfer conditions in the presence of KOH at room temperature to produce, respectively, vinyl-, (beta-phenylvinyl)-, and [beta-(trimethylsilyl)vinyl]aziridines in excellent yields within several minutes. In some cases, pyrroline compound 9 is obtained as a minor product. This aziridination reaction has also been carried out with preformed ylides, generated from sulfonium salts 3, 7, arsonium salt 14, and telluronium salts 15, 16 with a base in THF at -78 degrees C. In most examples, quantitative yields were achieved. However, the trans/cis selectivity of the reaction was not high in either case. A semistable allylic sulfonium ylide, i.e., dimethylsulfonium 3-(trimethylsilyl)allylide, was found to not undergo an expected [2,3]-sigma-rearrangement and so can also be used in this reaction. 相似文献
17.
Wan Pang Shifa Zhu Chunhui Xing Nianhua Luo Huanfeng Jiang Shizheng Zhu 《Journal of fluorine chemistry》2008,129(5):343-348
A series of stable fluorine-containing arsonium ylides and sulfur ylides were simply synthesized from perfluoroalkanesulfonyl diazocarbonyl compounds in the presence of rhodium catalyst. The ylide products are fairly stable due to the strong electron-withdrawing properties of perfluoroalkanesulfonyl group and carbonyl group. They are fully confirmed by spectral methods and the structures of 3ba and 3cd are also established by X-ray single crystal diffraction analysis. Several interesting features about the ylide structures and some weak fluorine interaction between them are described here. 相似文献
18.
A one-pot domino synthesis of photochromic 2,2-diarylphenanthro-(9,10)-[2H]-[1,4]-oxazines in excellent yield is described starting with acrylic acid derivatives. The reaction mechanism was studied by ReactIR and UV-vis. The cascade sequence of the reactions involves five transformations, namely, acyl azide formation, Curtius rearrangement, arsonium ylide formation, aza-Wittig, and final cyclization to the title compounds. 相似文献
19.
-cyclobutene forms a stable ylide with -tributylarsine. In contrast to the halogen cleavage of the analogous phosphonium ylide, which gives 1,1-dihaloalkanes, the arsonium ylide reacts with bromine and iodine to give the 1-halo--cyclobutenes. 相似文献
20.
α-Organoseleno arsonium ylide 3 was synthesized for the first time by a phenylselenenylation-transylidation reaction. It has sufficient activity to carry out the Wittig-type reaction, affording a novel method for the stereoselective synthesis of (Z)-α-phenyl-seleno-α, β-unsaturated esters 6. 相似文献