Oxidative cleavage of allyl ethers by an oxoammonium salt.

نویسندگان

  • Christopher B Kelly
  • John M Ovian
  • Robin M Cywar
  • Taylor R Gosselin
  • Rebecca J Wiles
  • Nicholas E Leadbeater
چکیده

A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.

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

A combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations.

The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using experimental and computational methods to gain deeper insight into trends in reactivity.

متن کامل

Polysulfones: solid organic catalysts for the chemoselective cleavage of methyl-substituted allyl ethers under neutral conditions.

The solid polysulfone made of SO2 and methylidenecyclopentane catalyzes the cleavage of methyl-substituted allyl ethers and liberates the corresponding alcohols.

متن کامل

SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations.

[reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.

متن کامل

Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands.

Rhodium complexes of diazaphospholane ligands catalyze the asymmetric hydroformylation of N-vinyl carboxamides, allyl ethers, and allyl carbamates; products include 1,2- and 1,3-aminoaldehydes and 1,3-alkoxyaldehydes. Using glass pressure bottles, short reaction times (generally less than 6 h), and low catalyst loading (commonly 0.5 mol %), 20 substrates are successfully converted to chiral ald...

متن کامل

New Aspects of Vinylsulfide Chemistry

Abstract: By utilizing the characteristic features of vinylsulfides, 2-(alkylthio)allyl silyl ethers were designed as efficient ene substrates, and their use led to exploration of general carbonyl and imine ene reactions. By using 3-(alkylthio)-2-siloxyallyl acetates, a useful [3 + 2]cyclopentane annulation methodology was developed. Further, a tandem CC bond formation/cleavage methodology was ...

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:
  • Organic & biomolecular chemistry

دوره 13 14  شماره 

صفحات  -

تاریخ انتشار 2015