Regioselectivity Control of the Ring Opening of Epoxides With Sodium Azide in a Microreactor

نویسندگان

  • Rajesh Munirathinam
  • Daejune Joe
  • Jurriaan Huskens
  • Willem Verboom
چکیده

The reaction of different types of aromatic and aliphatic epoxides with sodium azide to give vicinal azido alcohols was studied in a microreactor with and without pillars in the channels. Dependent on the substrate, the regioselectivity of the ring opening is affected by the used solvent system, viz. acetonitrile–water (sometimes with 10% acetic acid to promote the reactivity of substrates) or t-butyl acetate–water containing Tween80 as a surfactant. For styrene oxide and α-methylstyrene oxide, the α/β regioselectivity changes from 4 to 10 and 1.7 to 6.2, respectively, going from acetonitrile–water to Tween80-containing t-butyl acetate–water. The addition of a surfactant (Tween80) stabilizes the interface in the biphasic t-butyl acetate–water. Pillar-containing microreactors gave better conversions than microreactors without pillars and lab scale reactions, probably due to better mixing.

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

B-podands as efficient catalysts for the ring opening of epoxides in water: A versatile and atom economical method for the synthesis of vicinal azidoalcohols

For the first time B-podands have been studied as an efficient and powerful catalysts in the ring opening of epoxides with azide anion in water. The reaction afforded the corresponding 1,2-azidoalcohols with high regioselectivity under mild reaction conditions and in a highly atom economic fashion.

متن کامل

B-podands as efficient catalysts for the ring opening of epoxides in water: A versatile and atom economical method for the synthesis of vicinal azidoalcohols

For the first time B-podands have been studied as an efficient and powerful catalysts in the ring opening of epoxides with azide anion in water. The reaction afforded the corresponding 1,2-azidoalcohols with high regioselectivity under mild reaction conditions and in a highly atom economic fashion.

متن کامل

Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid.

Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.

متن کامل

Magnesium Oxide Nanoparticles for Catalytic Synthesis of 2-Substituted Alcohols from Regioselective Ring Opening of Epoxides in Water

Epoxides undergo regioselective ring opening with various nucleophiles using catalytic amount of nano magnesium oxide and water as solvent under mild reaction conditions. The remarkable features of this method are improved yields, high regioselectivity, and green chemistry agreement.

متن کامل

One-pot synthesis of highly regioselective β-azido alcohols catalyzed by Brønsted acidic ionic liquids

In this protocol, 3-(2-carboxybenzoyl)-1-methyl-1H-imidazol-3-ium chloride [Cbmim]Cl and sulfonic acid functionalized pyridinium chloride [pyridine-SO3H]Cl as a new, reusable, and green Brønsted acidic ionic liquid (BAIL) catalyst were synthesized and successfully used for the one-pot ring opening of epoxide with sodium azide (NaN3) in water at room temperature. Epoxides under ring-opening easi...

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   شماره 

صفحات  -

تاریخ انتشار 2012