- Acid-catalysed intramolecular addition of β-ketoesters to 1,3-dienes
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1,3-Dienyl β-keto esters are cyclised into bicyclolactones using the Bi(OTf)3/TfOH catalytic system. This reaction represents a rare case of simultaneous C-C and C-O bond formation at positions 1 and 3 of a 1,3-diene. Application to the synthesis of ramulosin is presented.
- Vayer, Marie,Fang, Weizhen,Guillot, Régis,Bezzenine-Lafollée, Sophie,Bour, Christophe,Gandon, Vincent
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Read Online
- Studies directed towards the total synthesis of aldosterone and naturally occurring analogues. A unified approach using the transannular Diels-Alder reaction
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A novel approach to the syntheses of aldosterone and naturally occurring analogues thereof is described. The strategy is characterized by a common and highly convergent route using the transannular Diels-Alder reaction of 14-membered TCC macrocyclic trien
- Couturier, Michel,Dory, Yves L.,Rouillard, Francois,Deslongchamps, Pierre
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Read Online
- Palladium-Catalyzed Tandem Hydrocarbonylative Lactamization and Cycloaddition Reaction for the Construction of Bridged Polycyclic Lactams
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The intramolecular hydroaminocarbonylation of alkenes is a compelling tool to rapidly access lactam, a privileged motif ubiquitous in natural products, pharmaceuticals, and agrochemicals. However, selective carbonylation to bridged polycyclic lactams with a lactam nitrogen at a bridgehead position is less explored. We herein report a modular palladium-catalyzed approach to perform a tandem hydrocarbonylative lactamization/Diels-Alder cycloaddition reaction with 2-vinyl aryl aldimines, alkenes, and CO, which offers convenient access to furnish the bridged polycyclic lactams in high yields with high selectivities.
- Xu, Pengcheng,Qian, Bo,Hu, Bin,Huang, Hanmin
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supporting information
p. 147 - 151
(2022/01/04)
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- PROCESS FOR SYNTHESIZING OF HYDROQUINONE DERIVATIVES WITH HEPTADECATRIENYL SIDE CHAIN
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Disclosed herein is a process for chemically synthesizing of hydroquinone derivatives, especially for hydroquinone derivatives with heptadecatrienyl side chain, which is synthesized via a Wittig reaction of 2-(10′-oxononyl)-1,4-diacetoxyl benzene and (3E,
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Paragraph 0032; 0045-0046
(2021/04/30)
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- HEPTADECATRIENE SIDE CHAIN HYDROQUINONE DERIVATIVE SYNTHESIS METHOD
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PROBLEM TO BE SOLVED: To provide a heptadecatriene side chain hydroquinone derivative synthesis method in which heptadecatriene side chain hydroquinone derivative being more stable than catechol and the final product being non-oily but solid can be synthe
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Paragraph 0027; 0029; 0044-0046
(2021/05/05)
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- Intramolecular N-Me and N-H aminoetherification for the synthesis ofN-unprotected 3-amino-O-heterocycles
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A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a va
- Paudyal, Mahesh P.,Wang, Mingliang,Siitonen, Juha H.,Hu, Yimin,Yousufuddin, Muhammed,Shen, Hong C.,Falck, John R.,Kürti, László
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supporting information
p. 557 - 560
(2021/02/06)
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- Phosphonium-based ionic liquids: Economic and efficient catalysts for the solvent-free cycloaddition of CO2 to epoxidized soybean vegetable oil to obtain potential bio-based polymers precursors
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A series of phosphonium-based ionic liquids have been prepared in one step in a simple way from inexpensive feedstocks. The prepared ionic liquids have been successfully tested as catalysts in the solvent-free cycloaddition reaction of CO2 to an epoxidized soybean oil to obtain carbonated soybean oil that can be potentially employed as bio-monomer in the synthesis for bio-based polymers. The catalytic performance of these ionic liquids was compared to the widely used and benchmark catalyst in CO2 cycloaddition to epoxides reaction, namely tetrabutylammonium bromide at different reaction conditions. The influence of some reaction parameters such as temperature, CO2 pressure, reaction time and catalyst amount was studied. It has been found that the solubility of the prepared ionic liquids in the reaction media (epoxidized soybean oil) is a key factor that limits the catalytic performance of some of the synthesized ionic liquids. All prepared ionic liquids have shown higher thermal stability that the benchmark catalyst and three of them have shown superior catalytic performance. The best results in terms of conversion and selectivity have been obtained with dodecyltriphenylphosphonium bromide (5) achieving almost full conversion (99.8%) and excellent selectivity (84.0%) after 5 h reaction at 160 oC and 40 bar of CO2. Outstanding results compared to those reported in the literature with similar catalysts in the solvent-free CO2 cycloaddtion to an epoxidized soybean oil to obtain the corresponding carbonated oil have been achieved. Considering the facile synthesis of catalyst 5, the large availability and non-expensive of the feedstocks and its catalytic performance it can be considered a valuable and green alternative for CO2 fixation to epoxidized vegetable oil.
- Centeno-Pedrazo, A.,Freixa, Z.,Garcia-Suarez, E. J.,Perez-Arce, J.,Prieto-Fernandez, S.
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- Cu-Catalyzed Regioselective C-H Alkylation of Benzimidazoles with Aromatic Alkenes
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Herein we report a novel Cu-catalyzed regioselective C2-H alkylation of benzimidazoles with aromatic alkenes. The reaction features exclusive regioselectivity and broad substrate scope in the intermolecular alkylation of benzimidazoles with terminal and i
- He, Yu-Ting,Mao, Yang-Jie,Hao, Hong-Yan,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian
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supporting information
p. 8250 - 8255
(2020/11/18)
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- Efficient synthetic methodology for the construction of dihydronaphthalene and benzosuberene molecular frameworks
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Benzosuberene analogues (1 and 2) and dihydronaphthalene analogues (3 and 4) function as potent inhibitors of tubulin polymerization, demonstrate pronounced cytotoxicity (low nM to pM range) against human cancer cell lines, and are promising vascular disrupting agents (VDAs). As such, these compounds represent lead anticancer agents with potential translatability towards the clinic. Methodology previously established by us (and others) facilitated synthetic access to a variety of structural and functional group modifications necessary to explore structure activity relationship considerations directed towards the development of these (and related) molecules as potential therapeutic agents. During the course of these studies it became apparent that the availability of synthetic methodology to facilitate direct conversion of the phenolic-based compounds to their corresponding aniline congeners would be beneficial. Accordingly, modified synthetic routes toward these target phenols (benzosuberene 1 and dihydronaphthalene 3) were developed in order to improve scalability and overall yield [45-57% (1) and 32% (3)]. Moreover, benzosuberene-based phenolic analogue 1 and separately dihydronaphthalene-based phenolic analogue 3 were successfully converted into their corresponding aniline analogues 2 and 4 in good yield (>60% over three steps) using a palladium catalyzed amination reaction.
- Mondal, Deboprosad,Niu, Haichan,Pinney, Kevin G.
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supporting information
p. 397 - 401
(2019/01/05)
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- Copper(I)-Catalyzed Enantioselective Intramolecular Aminotrifluoromethylation of O-Homoallyl Benzimidates
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In the present paper, the Cu(I)-catalyzed intramolecular aminotrifluoromethylation of O-homoallyl benzimidates with Togni reagent I was reported. O-Homoallyl benzimidates equipped with terminal alkenes produced chiral 1,3-oxazines with high enantioselectivity in the presence of a chiral BOX ligand, and racemic tetrahydro-1,3-oxazepines were obtained in high yields from internal alkene derivatives with a monoprotected amino acid additive under similar conditions.
- Mou, Xue-Qing,Rong, Feng-Ming,Zhang, Heng,Chen, Gong,He, Gang
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supporting information
p. 4657 - 4661
(2019/06/17)
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- Preparation and application of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide as new efficient ionic liquid catalyst for synthesis of 5-arylidene barbituric acids and pyrano[2,3-d]pyrimidine derivatives
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We report synthesis of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide ([TPPHSP]Br) as a reusable green Br?nsted-acidic ionic liquid catalyst and its application for synthesis of 5-arylidene barbituric acids and pyrano[2,3-d]pyrimidine derivatives by condensation reaction between aromatic aldehydes and barbituric acid or aromatic aldehydes, malononitrile, and barbituric acid in EtOH–H2O in reflux condition with good to excellent yield. The [TPPHSP]Br IL catalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR), and thermogravimetric (TG) analysis and showed good catalytic activity and reusability.
- Karami, Samira,Momeni, Ahmad Reza,Albadi, Jalal
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p. 3395 - 3408
(2019/04/25)
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- Compound, antibacterial finishing liquid, and preparation method and application of compound
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The invention provides a compound, antibacterial finishing liquid, and a preparation method and application of the compound. The general formula of the compound is shown in the description. The R1 ishalogen; the R2 is halogen, hydrogen, nitryl or heteroat
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Paragraph 0222-0226
(2019/06/30)
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- Precise delivery of therapeutic agents to cell mitochondria for anti-cancer therapy
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Described is a targeted molecular scaffold for construction of a metabolic inhibitor loaded with cancer-cell specific activity and anti-tumor immunity. Incorporation of a mitochondria targeting moiety such as triphenylphosphonium cation through a biodegra
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Page/Page column 2; 34
(2018/07/15)
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- A biosynthetically inspired route to substituted furans using the Appel reaction: Total synthesis of the furan fatty acid F5
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Appel reaction conditions have been harnessed to affect a mild biosynthetically inspired dehydration of endoperoxides to deliver multi-substituted electron rich furans. Unlike traditional dehydrative procedures, this method is metal and acid free, and can be achieved under redox neutral conditions. It is general for a range of aryl and alkyl substituted endoperoxides, and is functional group tolerant. Furthermore, this procedure has been used to deliver an effective total synthesis of the furan fatty acid (FFA) F5.
- Lee, Robert J.,Lindley, Martin R.,Pritchard, Gareth J.,Kimber, Marc C.
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supporting information
p. 6327 - 6330
(2017/07/11)
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- Nickel Catalyzed Regio-, Diastereo-, and Enantioselective Cross-Coupling of 3,4-Epoxyalcohol with Aryl Iodides
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The first catalytic, regioselective cross-coupling of 3,4-epoxyalcohol with aryl iodides is reported. The combination of NiCl2·DME and a newly developed C2-symmetric oxazoline ligand plays a key role in selective ring opening of seve
- Banerjee, Amit,Yamamoto, Hisashi
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supporting information
p. 4363 - 4366
(2017/08/23)
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- Mitochondria-targeted dihydropyridine derivative as well as preparation method and application thereof
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The invention discloses a preparation method and application of a mitochondria-targeted dihydropyridine compound. The mitochondria-targeted dihydropyridine compound has structures of a formula (I) and a formula (II) (shown in the description). Experiments prove that the mitochondria-targeted dihydropyridine compound is capable of effectively eliminating reactive oxygen species (ROS) generated by ionization radiation and therefore can be applied to the treatment of free radical-induced relevant diseases such as Alzheimer's disease and ionization damage disease. The preparation method is simple, and the product is easily prepared and pollution-free.
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Paragraph 0037
(2017/10/13)
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- Copper-Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans
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The copper-catalyzed intramolecular diastereoselective trifluoromethylcycloetherification of homoallylic alcohols with Togni's reagent as trifluoromethylating reagent was realized under mild conditions. Various trifluoromethylated tetrahydrofurans were synthesized in moderate to good yields. Moreover, a wide range of common functional groups was tolerated.
- Wang, Yanan,Jiang, Min,Liu, Jin-Tao
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supporting information
p. 1322 - 1327
(2016/04/26)
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- Rosmarinic acid derivative, preparation method and application
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The invention discloses a rosmarinic acid derivative, a preparation method and application. The rosmarinic acid derivative has the structure (please see the formula in the description) shown in the formula (I) or the formula (II). Experiments prove that t
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Paragraph 0031; 0040
(2016/10/10)
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- Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans
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We describe the design and development of the first catalytic asymmetric vinylogous Prins cyclization. This reaction constitutes an efficient approach for highly diastereo- and enantioselective synthesis of tetrahydrofurans (THFs) and is catalyzed by a confined chiral imidodiphosphoric acid (IDP). Aromatic and heteroaromatic aldehydes react with various 3,5-dien-1-ols to afford 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly excellent results when a highly acidic imidodiphosphorimidate (IDPi) catalyst is used. With a racemic dienyl alcohol, the reaction proceeds via a kinetic resolution. DFT calculations suggest an explanation for unusually high stereoselectivity.
- Xie, Youwei,Cheng, Gui-Juan,Lee, Sunggi,Kaib, Philip S.J.,Thiel, Walter,List, Benjamin
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supporting information
p. 14538 - 14541
(2016/11/18)
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- Design of a New Bimetallic Catalyst for Asymmetric Epoxidation and Sulfoxidation
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A new chiral tethered 8-quinolinol-based ligand class is developed. The binuclear titanium complex of the ligand operates through a novel mechanism allowing for the regio- and stereoselective epoxidation of primary and tertiary homoallylic alcohols (up to 98% ee), as well as first examples of 2-allylic phenols (up to 92% ee). The new catalyst system also promotes the asymmetric oxidation of γ-hydroxypropyl sulfides giving an important class of chiral sulfoxides that have been inaccessible to date (up to 95% ee).
- Bhadra, Sukalyan,Akakura, Matsujiro,Yamamoto, Hisashi
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supporting information
p. 15612 - 15615
(2016/01/09)
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- Phosphonium salts and aldehydes from the convenient, anhydrous reaction of aryl acetals and triphenylphosphine hydrobromide
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The reactions of aryl acetals/ketals and triphenylphosphine hydrobromide gave the corresponding aldehydes/ketones and alkyl phosphonium bromides. This reaction was applied to convert acetals/ketals to the corresponding aldehydes/ketones under an anhydrous
- Ramanathan, Mani,Hou, Duen-Ren
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- Remote functionalization of C60 with enantiomerically pure cyclo-[2]-malonate tethers bearing C12 and C14 spacers: Synthetic access to bisadducts of C60 with the inherently chiral trans-3 addition pattern
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In this Article, we describe the synthesis of two optically pure diols bearing a 1,2-diol moiety masked as an isopropylidene acetal group and long alkyl chains comprised of 12 and 14 carbon atoms, respectively. The synthetic methodology that was developed offers a general way for the synthesis of optically pure diols with long alkyl chains. Diols (-)-4 and (-)-9 were subjected to a condensation reaction with malonyl dichloride to afford two cyclo-[2]-malonate tethers that were separated by column chromatography in optically pure form. The bismalonates (-)-4b and (-)-9b proved to be excellent tethers for the regioselective Bingel functionalization of C60, furnishing in a regioselective manner the corresponding f,sC and f,sA trans-3 bisadducts with low diastereoselectivity but in very good to excellent total yields. In both cases, the formed trans-3 bisadducts were isolated in pure form by simple column chromatography and were fully characterized. The successful acetal deprotection of the synthesized trans-3 bisadducts afforded quantitatively the corresponding polyalcohols, which represent novel chiral fullerene compounds equipped with glycol moieties.
- Riala, Maria,Chronakis, Nikos
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p. 7701 - 7713
(2013/09/02)
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- Mitochondria-Targeted Inhibitors of Cytochrome C Peroxidase for Protection from Apoptosis
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The present application is directed to novel imidazole-substituted fatty acids that have been functionalized with an alkyl triphenylphosphonium group, compositions comprising these compounds and their use as inhibitors of cytochrome c peroxidase, in particular for the treatment and prevention of apoptosis.
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Paragraph 0173-0175
(2013/08/15)
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- Synthesis and in vitro pharmacological behavior of platinum(II) complexes containing 1,2-diamino-1-(4-fluorophenyl)-2-alkanol ligands
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In continuation of our effort to optimize the pharmacological profile of [1,2-diamino-1,2-bis(4-fluorophenyl)ethane]dichloridoplatinum(II) complexes, we synthesized [1,2-diamino-1-(4-fluorophenyl)alkanol]dichloridoplatinum(II) analogs. The aim of this study was to evaluate the influence of hydroxyl groups at the C2 moiety on aqueous solubility, lipophilicity, cellular platinum accumulation, and cytotoxicity against MDA-MB-231, U-937, RAJI, and SC-1 cells as well as against cisplatin-sensitive and cisplatin-resistant A2780 and A2780cisR ovarian carcinoma cells. As expected, the OH groups improved the water solubility and decreased the lipophilicity of the neutral ligands, resulting in complexes with favorable pharmacokinetic properties. The cellular uptake of the compounds in MDA-MB-231 and U-937 cells proved to depend on the configuration and showed only a slight correlation with lipophilicity. The most active complexes were R,R/S,S configured, which points to a carrier-mediated mode of action. [threo-1,2-Diamino-1-(4-fluorophenyl)propan]dichloridoplatinum(II) and [threo-2,3-diamino-3-(4-fluorophenyl)propan-1-ol]dichloridoplatinum(II) possessed only low cross-resistance to cisplatin and were up to 10-fold more active in lymphoma cell lines.
- Würtenberger, Irene,Angermaier, Bernhard,Kircher, Brigitte,Gust, Ronald
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supporting information
p. 7951 - 7964
(2013/11/06)
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- Asymmetric 5-endo chloroetherification of homoallylic alcohols toward the synthesis of chiral β-chlorotetrahydrofurans
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An asymmetric 5-endo chloroetherification of homoallylic alcohols is successfully developed that employs an easily available quaternary ammonium salt derived from cinchonine as a conventional organocatalyst. This approach provides ready access to β-chloro
- Zeng, Xianghua,Miao, Chengxia,Wang, Shoufeng,Xia, Chungu,Sun, Wei
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supporting information
p. 2418 - 2420
(2013/04/10)
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- ω-Thioacetylalkylphosphonium salts: Precursors for the preparation of phosphonium-functionalised gold nanoparticles
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Two new ω-thioacetylalkylphosphonium salts that function as masked cationic alkanethiolate ligands for the stabilisation of gold nanoparticles have been prepared. Both (3-thioacetylpropyl)triphenylphosphonium bromide and (6-thioacetylhexyl)triphenylphosphonium bromide were shown to form water-soluble gold nanoparticles of ca. 5-10 nm in size that are stable for up to six months. The related (3-thioacetylpropyl)diphenylphosphine oxide was also prepared but did not act as a stabilising ligand in gold nanoparticle formation.
- Ju-Nam, Yon,Allen, David W,Gardiner, Philip H.E.,Bricklebank, Neil
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body text
p. 3504 - 3508
(2009/02/05)
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- Phosphonioalkylthiosulfate zwitterions - New masked thiol ligands for the formation of cationic functionalised gold nanoparticles
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We report the synthesis and structural characterisation of a new family of stable phosphonioalkylthiosulfate zwitterions, R3P +(CH2)nS2O3- (R = Ph or Bu, n = 3,4,6, 8 or 10) which behave as cationic masked thiolate ligands with applications in the functionalisation of gold nanoparticles, having potential as new diagnostic biorecognition systems. The ligands were prepared by treatment of ω-bromoalkylphosphonium salts with sodium thiosulfate. The crystal and molecular structures of the zwitterions (R = Ph, n = 3) and (R = Bu, n = 3) were determined. A series of phosphonioalkanethiolate-capped gold nanoparticles dispersed in water was prepared by borohydride reduction of potassium tetrachloroaurate in the presence of the zwitterions in a dichloromethane-water system. UV-visible spectroscopy and scanning transmission electron-microscopy indicated that capped nanoparticles of ca. 5 nm diameter were present. The Royal Society of Chemistry 2006.
- Yon, Ju-Nam,Bricklebank, Neil,Allen, David W.,Gardiner, Philip H. E.,Light, Mark E.,Hursthouse, Michael B.
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p. 4345 - 4351
(2008/09/19)
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- Asymmetric synthesis of (-)-α-conhydrine
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The enantioselective synthesis of (-)-α-conhydrine has been achieved by two different synthetic routes. The key steps include Sharpless asymmetric dihydroxylation, regioselective opening of a cyclic sulfate and Wittig olefination.
- Kandula, Subba Rao V.,Kumar, Pradeep
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p. 3268 - 3274
(2007/10/03)
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- Synthesis of an isomer of the oxaspirobicyclic tetronic acid unit of the CCK-B receptor antagonist tetronothiodin
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An isomer of the oxaspirobicyclic tetronic acid unit of the CCK-B Receptor antagonist tetronothiodin, diastereoisomeric at the spiro centre, has been synthesized in five steps from dienol 4.
- Page, Philip C. Bulman,Vahedi, Hooshang,Batchelor, Kevin J.,Hindley, Stephen J.,Edgar, Mark,Beswick, Paul
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p. 1022 - 1024
(2007/10/03)
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- Epoxidation of peptidyl olefin isosteres. Stereochemical induction effect of chiral centers at four adjacent C(α) positions
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Four tripeptidyl olefin isosteres were prepared, each of which contains a single chiral center derived from the bulky amino acid phenylalanine at positions corresponding to the P2-P'2 positions of a protease substrate. The effect of these chiral centers on the stereochemical outcome of mCPBA epoxidation of the olefin functionality was studied. A chiral center at P2 or P'2 position has no significant effect, and the P'1 position exerts a small stereoselectivity. A chiral center at the P1 position, on the other hand, has a profound chiral induction effect on the epoxidation reaction. (C) 2000 Elsevier Science Ltd.
- Perlman, Nurit,Livneh, Mordechai,Albeck, Amnon
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p. 1505 - 1516
(2007/10/03)
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- Hypolipidaemic compounds
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The invention provides novel 1,4-benzothiazepine compounds substituted with hydroxy or a group containing hydroxy, compositions comprising such compounds and their use in the treatment or prophylaxis of treating clinical conditions in which inhibition of bile acid uptake is indicated, for example, hyperlipidemia and atherosclerosis.
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- 2,3-Epoxy-10-aza-10,11-dihydrosqualene, a High-Energy Intermediate Analogue Inhibitor of 2,3-Oxidosqualene Cyclase
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2,3-Epoxy-10-aza-10,11-dihydrosqualene, a high-energy intermediate analogue inhibitor of 2,3-xidosqualene (SO) cyclase was obtained by total synthesis.This involved the preparation of three main building blocks: (1) C17 squalenoid N-methylamine, (2) 3-(diphenylphosphinoyl)propanal, and (3) 5,6-epoxy-6-methylheptan-2-one.The final stages of the reconstruction of the 6E double bond were obtained by a Wittig-Horner reaction which was modified for poorly reactive systems.This compound was designed to mimic the C-8 carbonium ion formed during SO cyclization.Its inhibitory activity on various SO cyclases was evaluated and compared with the 6 Z isomer which has an unfavorable geometry.Only isomer 6 E, the carbocation analogue, was active on SO cyclases from rat liver, pig liver, S. cerevisiae, and C. albicans microsomes, with an I50 varying from 3 to 5 μM.Both E and Z isomers were inactive on squalene epoxidase at the higher concentrations tested.
- Ceruti, Maurizio,Balliano, Gianni,Viola, Franca,Grosa, Giorgio,Rocco, Flavio,Cattel, Luigi
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p. 3050 - 3058
(2007/10/02)
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- Investigation of Aliphatic Dienes by Chemical Ionization with Nitric Oxide
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It is shown that the position of the double bond close to the hydrocarbon end of an aliphatic diene functionalized at C(1) can readily be determined by chemical ionization with NO+.Owing to the low abundance of the ions characteristic for the position of the other double bond, its localization may be difficult.Measurement of the chemical ionization (nitric oxide as reagent gas) spectra of the corresponding epoxides or collision activation studies can help.
- Budzikiewicz, H.,Blech, St.,Schneider, B.
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p. 1057 - 1060
(2007/10/02)
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- A New Identification Method for Aliphatic Compounds Using Linear Equations of the GC Retention Index Value
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The Retention Index (I) value and the different I values from two columns, carbowax 20M (20M) and OV101 (ΔI:I20M-IOV101) of aliphatic compounds were calculated by several kinds of linear equations under programmed linear temperature conditions.The equations could be used to predict appropriate compounds as well as a database of I and ΔI values.
- Tamura, Hirotoshi,Kihara, Shingo,Sugisawa, Hiroshi
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p. 3171 - 3176
(2007/10/02)
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- ACYL TRANSFER REACTIONS WITH PHOSPHINE OXIDES: SYNTHESIS OF E-HOMOALLYLIC ALCOHOLS, CYCLOPROPYL KETONES, AND γ-HYDROXY KETONES
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Esters of 3-hydroxypropylphosphine oxides rearrange in base by O to C acyl (RCO) transfer to give the hydroxy ketones (8). threo-Selective reduction of (8) leads to pure E-homoallylic alcohols whilst C to O acyl )Ph2PO) transfer leads to γ-hydroxy ketones with nucleophilic aqueous base or cyclopropyl ketones with BuOKt - HOBut.
- Wallace, Paul,Warren, Stuart
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p. 2971 - 2978
(2007/10/02)
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