Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions.

Org Biomol Chem

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA.

Published: February 2016

Alcohols are effectively converted to their corresponding diphenylmethyl (DPM) ethers by reaction with O-diphenylmethyl trichloroacetimidate in refluxing toluene without the requirement of a catalyst or other additives. A number of acid and base sensitive substrates were protected in excellent yield using this new method without disturbing the pre-existing functionality present in these molecules. This reaction is the first example of the formation of an ether from stoichiometric amounts of a trichloroacetimidate and an alcohol without the addition of a Brønsted or Lewis acid catalyst.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4986612PMC
http://dx.doi.org/10.1039/c5ob02455bDOI Listing

Publication Analysis

Top Keywords

dpm ethers
8
o-diphenylmethyl trichloroacetimidate
8
formation dpm
4
ethers o-diphenylmethyl
4
trichloroacetimidate thermal
4
thermal conditions
4
conditions alcohols
4
alcohols effectively
4
effectively converted
4
converted corresponding
4

Similar Publications

Physicochemical and biological evaluation of 'click' synthesized vinyl epoxide-chitosan film for active food packaging.

Int J Biol Macromol

December 2024

Polymer Research Laboratory, Department of Chemistry, Motilal Nehru National Institute of Technology Allahabad, Prayagraj 211004, Uttar Pradesh, India. Electronic address:

Chitosan (Cs) being a natural biopolymer serves as an excellent template to construct active packaging materials for achieving sustainable development. In this study, Cs was chemically modified via epoxide ring opening click reaction using vinyl epoxide to obtain a novel chitosan vinyl epoxide (Cs-VE) derivative with hydroxyl and olefinic functional groups. The Cs-VE transparent film was fabricated through the eco-friendly solution casting technique.

View Article and Find Full Text PDF

Improving the Performance of Si/PEDOT:PSS Hybrid Solar Cells with More Economical and Environmentally Friendly Alcohol Ether Solvents.

ACS Omega

April 2024

International Joint Research Center for Optoelectronic and Energy Materials, School of Materials and Energy, Yunnan University, Kunming, Yunnan 650091, China.

The photoelectric characteristics of poly(3,4-ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS) films significantly affect the power conversion efficiency and stability of Si/PEDOT:PSS hybrid solar cells. In this paper, we investigated PEDOT:PSS modification with alcohol ether solvents (dipropylene glycol methyl ether (DPM) and propylene glycol phenyl ether (PPH)). The reduction of PSS content and the transformation of the PEDOT chain from benzene to a quinone structure in PEDOT:PSS induced by doping with DPM or PPH are the reasons for the improved conductivity of PEDOT:PSS films.

View Article and Find Full Text PDF

Facile synthesis and anion binding studies of fluorescein/benzo-12-crown-4 ether based bis-dipyrromethane (DPM) receptors.

RSC Adv

October 2023

Organic and Supramolecular Functional Materials Research Laboratory, Department of Chemistry Jamia Millia Islamia, Okhla New Delhi 110025 India +91-7011867613.

Two novel fluorescein as well as benzo-12-crown-4 ether functionalized dipyrromethane receptors (DPM3 and DPM4) have successfully been synthesized. The anion (used as their TBA salts) binding studies of thus prepared DPM3 and DPM4 receptors were evaluated by the UV-visible spectrophotometric titrations. Binding affinities as well as the stoichiometry were determined through the UV-visible titrations data with the involvement of the BindFit (v0.

View Article and Find Full Text PDF

Practical preparation of diphenylmethyl ethers from 2-diphenylmethoxypyridine using catalytic iron(iii) chloride.

Org Biomol Chem

June 2019

Department of Nuclear Medicine, Molecular Imaging & Therapeutic Medicine Research Center, Chonbuk National University Medical School and Hospital, Jeonju, 54907, Republic of Korea.

A novel facile synthetic method for producing diphenylmethyl (DPM) ethers from 2-diphenylmethoxypyridine was developed. A variety of DPM ethers was successfully achieved with high yield via treatment of alcohols with 2-diphenylmethoxypyridine in the presence of catalytic FeCl3. The procedure is a practical and efficient synthetic procedure to protect various alcohols, and it can be applied to prepare bioactive compounds.

View Article and Find Full Text PDF

The series of chelating phosphine ligands, which contain bidentate P (bis[(2-diphenylphosphino)phenyl] ether, DPEphos; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, Xantphos; 1,2-bis(diphenylphosphino)benzene, dppb), tridentate P (bis(2-diphenylphosphinophenyl)phenylphosphine), and tetradentate P (tris(2-diphenylphosphino)phenylphosphine) ligands, was used for the preparation of the corresponding dinuclear [M(μ-SCN)P] (M = Cu, 1, 3, 5; M = Ag, 2, 4, 6) and mononuclear [CuNCS(P/P)] (7, 9) and [AgSCN(P/P)] (8, 10) complexes. The reactions of P with silver salts in a 1:2 molar ratio produce tetranuclear clusters [Ag(μ-SCN)(t-SCN)(P)] (11) and [Ag(μ-SCN)(P)] (12). Complexes 7-11 bearing terminally coordinated SCN ligands were efficiently converted into derivatives 13-17 with the weakly coordinating SCN:B(CF) isothiocyanatoborate ligand.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!