36441-31-3Relevant articles and documents
Influence of phase transfer catalyst structure on selectivity
Dehmlow, E. V.
, p. 1998 - 2005 (1995)
A concise review is given of systematic studies concerned with the tuning of regio-, "frequentio-", chemo-, and diastereoselectivity by the structure or type of phase transfer catalyst. - Keywords: phase transfer catalysis; regioselectivity; selectivity control; stereoselectivity; C/O-alkylation; C/N-alkylation.
Ionic liquids as solvents for the regioselective O-alkylation of C/O ambident nucleophiles
Badri, Meryam
, p. 4435 - 4438 (1992)
The reaction of sodium β-naphthoxide with benzyl halides in molten tetraalkylammonium or phosphonium halides (at 110°C or below) leads to a highly regioselective O-alkylation. These new solvents, which can be quantitatively recovered at the end of the reaction, mimic the behaviour of dipolar aprotic solvents.
HIGHLY SELECTIVE BENZILATIONS OF β-NAPHTHOXIDE ANION IN HETEROGENEOUS MEDIA
Bram, G.,Loupy, A.,Sansoulet, J.,Vaziri-Zand, F
, p. 5035 - 5038 (1984)
Each of the four products resulting from the benzylation of the ambident β-naphthoxide anion can be efficiently and selectively obtained in mild an economical conditions by a judicious choice of the solid base: LiOH, LiOtBu or KOH-Aliquat.
THE ROLE HYDROGEN BONDING IN THE AUTOOXIDATION AND ALKYLATION OF 2-NAPHTHOLS
Jazzaa, Abdulaziz Al,Clark, James H.,Miller, Jack M.
, p. 89 - 92 (1983)
The powerful hydrogen bond electron donor fluoride ion assists the O-alkylation of 2-naphthols but inhibits the autooxidation of 1-alkyl-2-naphthols.These observations may be explained in terms of the nature of the OHF- hydrogen bond.
Mechanism of Reactions Promoted by Polymer-Supported Phase-Transfer Catalysts
Montanari, Fernando,Quici, Silvio,Tundo, Pietro
, p. 199 - 202 (1983)
Kinetic measurements indicate that the ratio of C- vs.O-alkylation of β-naphthoxide is not a reliable polarity test for polymer-supported phase-transfer catalysis because of the competitive noncatalyzed reactions.A reliable test is the C/O-alkylation of phenoxide.Reactions carried out in toluene-water in the presence of stoichiometric amounts of polystyrene-supported quaternary phosphonium salts 2 and 3 afford only O-alkylation products.Stoichiometric reactions give significant amounts of C-alkylation with 2 or 3 in aqueous ethanol or with immobilized polar catalysts 4 and 5 in toluene-water.Hydration measurements agree with the essentially hydrophobic character of polystyrene-supported phosphonium catalysts 2 and 3.These results confirm our previous conclusion that phase-transfer catalysis follows identical mechanisms both in the presence of soluble and polymer-supported catalysts.In the latter case the reaction should occur within an organic solvation shell firmly surrounding the catalytic site, rather than in an aqueous solvation sphere or at the interface.
Catalytic Tandem and One-Pot Dehydrogenation-Alkylation and -Insertion Reactions of Saturated Hydrocarbons with Alcohols and Alkenes
Kim, Junghwa,Pannilawithana, Nuwan,Yi, Chae S.
, p. 8395 - 8398 (2016/12/16)
The ruthenium-hydride catalyst has been successfully used for the tandem sp3 C-H dehydrogenation-alkylation reaction of saturated hydrocarbon substrates with alcohols to form the alkyl-substituted alkene and arene products. The analogous one-pot dehydrogenation-insertion of saturated ketones with alkenes and dienes directly yielded synthetically useful 2-alkylphenol and benzopyran products in a highly regio- and stereoselective manner without forming any wasteful byproducts. (Chemical Equation Presented).
6-HYDROXY-2-NAPHTHALENYL FLUORENE DERIVATIVES AND LENS AND CAMERA MODULE USING THE SAME
-
, (2016/02/16)
Disclosed herein are 6-hydroxy-2-naphthalenyl fluorene derivatives and a lens and a camera module using the same.
Microwave-Assisted solid-liquid phase alkylation of naphthols
Balint, Erika,Kovacs, Orsolya,Drahos, Laszlo,Keglevich, Gyoergy
, p. 330 - 336 (2013/07/26)
The microwave promoted alkylation of 1- and 2-naphthols with benzyl, butyl, ethyl and isopropyl halides in the presence of an alkali carbonate may result in O- and C-Alkylated products. The alkylations were O-selective in the presence of K2CO3 in acetonitrile as the solvent and in the absence of phase transfer catalyst. The alkylations utilizing butyl and ethyl halides were also O-selective in solventless accomplishment and in the presence of triethylbenzylammonium chloride.
An efficient method for the preparation of versatile building blocks: 1-substituted 2,2-dimethoxyethylamine hydrochlorides1
Liu, Bo,Su, Deyong,Cheng, Guolin,Liu, Hui,Wang, Xinyan,Hu, Yuefei
scheme or table, p. 3227 - 3232 (2010/02/27)
A novel method for the preparation of 1-substituted 2,2-dimethoxyethylamine hydrochlorides was developed. The method includes three highly efficient steps: (1) direct use of aqueous (MeO)2CHCHO for the preparation of N,O-acetal by condensation with Betti
Convenient synthesis of 1-arylmethyl-2-naphthols
Paul, Nawal K.,Dietrich, Lindsay,Jha, Amitabh
, p. 877 - 888 (2007/10/03)
A new environmentally benign, two-step procedure for the synthesis of 1-arylmethyl-2-naphthols in good to excellent yield is reported. It involves microwave-assisted facile formation of Mannich bases of 2-naphthol under solvent-free conditions and subsequ
