- Ball-Milling-Enabled Reactivity of Manganese Metal**
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Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.
- Bolt, Robert R. A.,Browne, Duncan L.,Howard, Joseph L.,Khan, Adam,Magri, Giuseppina,Morrill, Louis C.,Nicholson, William I.,Richards, Emma,Seastram, Alex C.
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supporting information
p. 23128 - 23133
(2021/09/20)
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- Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols
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Since esters are important organic synthesis intermediates, an environmentally friendly oxone catalyzed-esterification of carboxylic acids with alcohols has been developed. A series of carboxylic acid esters are obtained in high yield. This strategy requires mild reaction conditions, providing an attractive alternative for the construction of valuable carbonyl esters. Electron-rich and electron-deficient groups are compatible with the standard conditions and a variety of substrates are demonstrated. Moreover, the reaction could easily be adapted to typical prodrugs, drugs and gram-scale synthesis.
- Hou, Fei,Wang, Xi-Cun,Quan, Zheng-Jun
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supporting information
p. 9472 - 9476
(2019/01/03)
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- Preparation method of malonic ester
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The invention provides a preparation method of malonic ester. Malonic ester is obtained by using 70-80 wt% of cyanoacetic acid, hydrogen chloride-alcoholic solution and corresponding alcohol as raw materials, and is subjected to the process of esterification, dealcoholic water, alcoholysis esterification, dealcoholization, neutralization and distillation. The preparation method chooses the cyanoacetic acid of reasonable concentration, reduces the heat-sensitive reaction of distillation dehydration when obtaining high concentration cyanoacetic acid, and reduces the difficulty of dehydration ofthe cyanoacetic acid raw materials; the method is high in operability, reasonable and economy, reduces the discharge of three wastes greatly, and has good social benefit.
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Paragraph 0059-0068
(2018/04/01)
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- 1,5-Diketones Synthesis via Three-Component Cascade Reaction
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A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.
- Xing, Li-Juan,Lu, Tao,Fu, Wei-Li,Lou, Mei-Mei,Chen, Bo,Wang, Zhi-Shen,Jin, Yang,Li, Dan,Wang, Bin
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supporting information
p. 3076 - 3080
(2015/11/03)
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- Transformation of amides into esters by the use of chlorotrimethylsilane
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A mild transformation of various amides and imides into the corresponding esters and diesters in good yields by using chlorotrimethylsilane and alcohols at rt are described. Either primary, secondary, or tertiary amide or imide can be used in this transformation. Primary and secondary alcohols gave better yields than tertiary alcohols.
- Xue, Cuihua,Luo, Fen-Tair
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p. 359 - 362
(2015/02/02)
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- Catalytic asymmetric conjugate allylation of coumarins
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A catalytic asymmetric conjugate allylation was successfully developed to synthesize potential pharmacologically active 4-allyl-2-oxochroman skeletons. A dual activation strategy was employed by using N,N′-dioxide-Yb(OTf) 3 to activate coumarins and using (CuOTf)2?C 7H8 to activate tetraallyltin via transmetalation, respectively. Good yields and enantioselectivities were obtained under mild conditions.
- Kuang, Yulong,Liu, Xiaohua,Chang, Lu,Wang, Min,Lin, Lili,Feng, Xiaoming
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supporting information; experimental part
p. 3814 - 3817
(2011/09/15)
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- A facile, catalytic and environmentally benign method for esterification of carboxylic acids and transesterification of carboxylic esters with nearly equimolar amounts of alcohols
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A practical and green chemical process for the esterification of carboxylic acids with alcohols and transesterification of carboxylic esters in good to excellent yields by using K5CoW12O14· 3H2O (0.1 mol%) as catalyst is reported. The catalyst exhibited remarkable reusable activity. Georg Thieme Verlag Stuttgart.
- Bose, D. Subhas,Satyender, Apuri,Das, A. P. Rudra,Mereyala, Hari Babu
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p. 2392 - 2396
(2008/02/08)
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- Micelle composition of polymer and passenger drug
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Hydrophobic drugs become more practical for treatments by being encapsulated in micelle compositions for increasing solubility. Micelle compositions may include an excipient tocopherol and/or prodrug formulations of the drug. Micelles extend the time period the drug remains in the micelles to improve drug circulation time and thereby drug delivery. Hydrophobic drugs for micelle encapsulation may include rapamycin, geldanamycin, and paclitaxel. Administration of these micelle compositions does not require Cremophor EL or Tween 80, avoiding serious side effects associated with these products which would previously accompany such drug administration.
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Page/Page column 8; fig.47; sheet 21
(2010/11/24)
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- Catalytic electronic activation as a tool for the addition of stabilised nucleophiles to allylic alcohols
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This paper describes the activation of 2-cyclohexen-1-ol (1) and 2-cyclopenten-1-ol (11) through the use of aluminium-catalysed transfer hydrogenation. The electronically activated substrates are demonstrated to undergo facile conjugate addition and, when the alcohol functional group is subsequently restored in a one-pot procedure, this leads to an indirect addition of nucleophiles to allylic alcohols. This novel methodology has been termed catalytic electronic activation. The aluminium tert-butoxide catalysed conversion of 2-cyclohexen-1-ol (1) into 2-(3-hydroxycyclohexyl)-2- methylmalononitrile (18) and 2-cyclopenten-1-ol (11) into 2-(3- hydroxycyclopentyl)-2-methylmalononitrile (16) in 90 and 60% yield, respectively has been demonstrated through an efficient domino Oppenauer/Michael addition/Meerwein-Ponndorf-Verley process.
- Black, Phillip J.,Edwards, Michael G.,Williams, Jonathan M.J.
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p. 1363 - 1374
(2007/10/03)
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- Transformation of amides into esters by the use of chlorotrimethylsilane
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A mild transformation of various amides and imides into the corresponding esters and diesters in good yields by using chlorotrimethylsilane and alcohols at rt are described. Either primary, secondary, or tertiary amide or imide can be used in this transformation. Primary and secondary alcohols gave better yields than tertiary alcohols.
- Xue, Cuihua,Luo, Fen-Tair
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p. 359 - 362
(2007/10/03)
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- One-Pot synthesis of 5-Alkylthio-3H-1,2-dithiole-3-thiones: Advantages and scopes
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The reaction of dialkyl malonate esters with P2S5/S8 in boiling xylene in the presence of 2-mercaptobenzothiazole/ZnO as catalyst produces 5-alkylthio-3H-1,2-dithiole-3-thiones as major identifiable product. Moderate yields were obtained with malonate esters of primary alcohols. The reaction fails with malonate esters of secondary alcohols. Regarding the substituent in position two, dialkyl malonates with groups such as CH3, Ph, CH2Ph, OCH3 and Cl afford the corresponding 4-substituted derivatives whereas with Br and NO2 do not give the expected products. Some mechanistic evidences are described.
- Aimar,De Rossi
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p. 1749 - 1755
(2007/10/03)
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- CHEMISTRY OF NITRO ESTERS XVII. METHOD FOR THE PRODUCTION OF MESOXALIC ESTERS
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A new preparative method was developed for the production of mesoxalic esters from bromomalonic esters and silver nitrate
- Kochergin, P. M.,Titkova, R. M.
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p. 1042 - 1044
(2007/10/02)
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- A Mild, Simple, and Convenient Synthesis of Diesters from Malonyl or Succinyl Dichloride and Alcohols Catalyzed by Potassium Tetracarbonylhydridoferrate, KHFe(CO)4, as a New Catalyst
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A large variety of alcohols react with acyl halides of dicarboxylic acids such as malonyl dichloride and succinyl dichloride in the presence of a catalytic amount of tetracarbonylhydridoferrate at room temperature under carbon monoxide or nitrogen to give the corresponding diesters in good yields.
- Shim, Sang Chul,Huh, Keun Tae,Park, Woo Hyun
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- Process for the preparation of 3,5-dihydrocarbyl-4-hydroxybenzylmalonic acid esters
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Esters of 3,5-dihydrocarbyl-4-hydroxybenzylmalonic acid are prepared by reacting a 2,6-dihydrocarbyl-4-halomethylphenol with an ester of a 1,3-dicarboxylic acid in the presence of an alkali or an alkaline earth metal hydride. The products are useful as antioxidants.
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- Method of preparing malonic acid dialkyl esters
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Production of malonic acid dialkyl esters by reacting halogen acetic acid alkyl ester with carbon monoxide, and alkali alcoholate, alkali earth alcoholate or a solution of alkali hydroxide in an alcohol at a pH of up to 8.5 in the presence of a cobalt compound which is a catalyst for the reaction.
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