Oxidation of Secondary Methyl Ethers to Ketones

نویسندگان

  • Pieter J. Gilissen
  • Daniel Blanco-Ania
  • Floris P. J. T. Rutjes
چکیده

We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketones in up to 98% yield. The use of this methodology could expand the application of the methyl group as a useful protecting group.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Experimental study of the oxidation of methyl oleate in a jet-stirred reactor.

The experimental study of the oxidation of a blend containing n-decane and a large unsaturated ester, methyl oleate, was performed in a jet-stirred reactor over a wide range of temperature covering both low and high temperature regions (550-1100 K), at a residence time of 1.5 s, at quasi atmospheric pressure with high dilution in helium (n-decane and methyl oleate inlet mole fractions of 1.48 ×...

متن کامل

Accurate Prediction of Thermodynamic Properties of Alcoholes Ketones and Ethers by MCORGC Eos

This paper presents the ability of a new group contribution equation of state in the prediction of thermodynamic properties of alcohols, ketones and ethers. This equation of state, called MCORGC, is based on the Chain-Of-Rotators Group Contribution equation considering a NRTL type local composition mixing rule. The group parameters required to predict the thermodynamic properties of the oxygena...

متن کامل

Hydrocarbon oxidation catalyzed by self-folded metal-coordinated cavitands.

Functionalized cavitands have been shown to self-fold via coordination of Fe(II) salts and effect catalytic C-H oxidation reactions of unfunctionalized alkanes under mild aqueous conditions in the presence of tert-butyl hydroperoxide as co-oxidant. Secondary and tertiary C-H bonds can be converted to ketones and alcohols, respectively, and ethers can be converted to esters. The cavitands retain...

متن کامل

Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols

Following an optimized multicomponent procedure, an aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs under mild conditions by mediation of the TiCl4/Zn/t-BuOOH system, leading to the formation of quaternary β-amino-ethers and -alcohols. The n...

متن کامل

A stabilized formulation of IBX (SIBX) for safe oxidation reactions including a new oxidative demethylation of phenolic methyl aryl ethers.

[reaction: see text] SIBX is a nonexplosive formulation of IBX that can be used as a suspension in a variety of standard organic solvents such as refluxing EtOAc and THF to oxidize safely alcohols into aldehydes and ketones. The use of hot THF is limited to the oxidation of allylic and benzylic alcohols. Most yields are comparable to those obtained with IBX or DMP. SIBX can also be used to perf...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره 82  شماره 

صفحات  -

تاریخ انتشار 2017