104-52-9Relevant articles and documents
An efficient method for chlorination of alcohols using PPh3/Cl3CCONH2
Pluempanupat, Wanchai,Chavasiri, Warinthorn
, p. 6821 - 6823 (2006)
A new and convenient method for the chlorination of alcohols utilizing PPh3/Cl3CCONH2 is addressed. Various alcohols could smoothly be converted into their corresponding alkyl chlorides in high yield under mild conditions with short reaction times. A mechanism is disclosed with the evidence of inversion of configuration of the analogous alkyl chloride derived from R-(-)-2-octanol.
Indium(III)-catalyzed reductive bromination and iodination of carboxylic acids to alkyl bromides and iodides: Scope, mechanism, and one-pot transformation to alkyl halides and amine derivatives
Moriya, Toshimitsu,Yoneda, Shinichiro,Kawana, Keita,Ikeda, Reiko,Konakahara, Takeo,Sakai, Norio
, p. 10642 - 10650 (2013)
Highly effective indium(III)-catalyzed reductive bromination or iodination of a variety of carboxylic acids with 1,1,3,3-tetramethyldisiloxane (TMDS) and a source of bromine or iodine is described. This functional group interconversion has high tolerance for several functional groups, such as halogens, a hydroxy group, a nitro group, an olefin part, and a sulfide moiety. This indium catalytic system is also applicable to the reductive iodination of aldehyded, acyl chlorides, and esters. Furthermore, this reducing system can be applied to the one-pot synthesis of alkyl halides and amine derivatives via the addition of nucleophiles. Insight into the reaction mechanism was gained via the time course of 1H and 13C NMR monitoring experiments and the corresponding stepwise reactions.
Remarkable interaction effects of molecular packing on site- and stereoselectivity in photocycloaddition of 2-pyrones with maleimide in the solid state
Obata, Toru,Shimo, Tetsuro,Yasutake, Mikio,Shinmyozu, Teruo,Kawaminami, Masaru,Yoshida, Ryosuke,Somekawa, Kenichi
, p. 1531 - 1541 (2001)
Solid-state photoirradiation of 1:1 complex crystals of 4-[ω-(2-furyl)alkyloxy]-6-methyl-2-pyrones 1b, 1c or 4-(ω-arylalkyloxy)-6-methyl-2-pyrones 1d-j with maleimide 2 gave [2+2]cycloadducts 3b-f, 3i, 3j with exclusive stereoselectivity. The high reaction selectivity was confirmed by X-ray structure analyses and MO method of the complex crystals, which were composed of two sets of a 1:1 complex between 1 and 2, arising from an CH-π interaction between 2 and the aromatic rings of 1, and/or π-π stacking between the aromatic rings in addition to four kinds of hydrogen bonding between the ground state 2-pyrone moieties and 2.
Synthesis, crystal structure, and fluorescence properties of a novel coordination polymer [Zn(L)(4,4'-bipyridine)(H2O)] n ·(H2O) 4
Gao,Wang,Lin,Liu,Sun,Zhu
, p. 386 - 391 (2012)
In this work, a novel and rare coordination polymer, [Zn(L)(Bipy)(H 2O)] n ·(H2O) 4 (H 2L-sphe-nylpropylmalonate acid, Bipy-4,4'-bipyridine), has been synthesized and characterized by elemental analysis, FT-IR spectroscopy, and solid fluorimetry studies. In the crystal, the Zn2+ ion of the complex is hexa-coordinated in a slightly distorted octahedral configuration forming the unit structure, 2D structure, and 3D framework. The supramolecular architecture was constructed by a unit of (H2O) 4 discrete water cluster. Besides, the coordination polymer displays strong emission spectra due to the metal-to-ligand charge-transfer transition, having potential applications as fluorescent materials. Pleiades Publishing, Ltd., 2012.
Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene
Chen, Kun-Quan,Wang, Zhi-Xiang,Chen, Xiang-Yu
, p. 8059 - 8064 (2020)
While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters
André-Joyaux, Emy,Kuzovlev, Andrey,Renaud, Philippe,Tappin, Nicholas D. C.
, p. 13859 - 13864 (2020/06/10)
The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.
Preparation method of 3-phenylpropylamine
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Page/Page column 4-6, (2019/10/08)
The embodiment of the invention discloses a preparation method of 3-phenylpropylamine. The method comprises the following steps: 2-(3-phenylpropyl)isoindoline-1,3-diketone is obtained through 1-chloro-3-phenylpropane under the action of a phthalimide salt compound and a base; then the 2-(3-phenylpropyl)isoindoline-1,3-diketone is subjected to hydrazinolysis through hydrazine hydrate; after alkalization, recrystallization is performed to obtain the 3- phenylpropylamine. According to the preparation method of the 3-phenylpropylamine disclosed by the embodiment of the invention, 3- phenylpropanol is used as a raw material, substitution reaction is performed to obtain the 1-chloro-3-phenylpropane, the 1-chloro-3-phenylpropane is reacted with the phthalimide salt to obtain the 2-(3-phenylpropyl)isoindoline-1,3-diketon, and then hydrazine hydrate hydrolysis is performed to obtain the 3-phenylpropylamine. The preparation method disclosed by the embodiment of the invention has the beneficial effects that the raw material required is cheap and easy to obtain, the reaction conditions are simple, the operation is simple and convenient, the toxicity and the pollution are small, the yield and the purity are high, and the method is suitable for industrial production.
Ionic-Liquid-Supported 1,3-Dimethylimidazolidin-2-one: Application as a Reusable Halogenation Reagent
Koguchi, Shinichi,Shibuya, Yuga,Igarashi, Yusuke,Takemura, Haruka
supporting information, p. 943 - 946 (2019/05/10)
We describe the synthesis of ionic-liquid-supported 1,3-dimethylimidazolidin-2-one, together with the halogenation of alcohols in a reaction system in which this reagent is combined with oxalyl chloride. A new method was established that does not require additives such as bases, and which permits the ready isolation and purification of the product. Good conversions were obtained, and good reusability of the reagent was observed.
Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling
Longwitz, Lars,Jopp, Stefan,Werner, Thomas
, p. 7863 - 7870 (2019/06/27)
A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g., no additional solvent is required and the phosphane reagent is used only in catalytic amounts. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in yields up to 95%. Under optimized conditions, it was also possible to convert epoxides and an oxetane to the dichlorinated products.
