Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides

نویسندگان

  • Akihiro Shimizu
  • Ryutaro Hayashi
  • Yosuke Ashikari
  • Toshiki Nokami
  • Jun-ichi Yoshida
چکیده

β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br(+) and I(+) ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.

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

Disulfide catalyzed the highly regioselective conversion of epoxides to halohydrins with elemental halogens

The regioselective ring opening of styrene oxide using elemental iodine and bromine in the presence of disulfides as new catalysts was studied. The conductivity titration and UV spectroscopy were used to study the interaction of iodine with these catalysts. The results indicate that disulfide 11 is efficient in polyiodide formation, and can catalyze this reaction in excellent yield and high reg...

متن کامل

Disulfide catalyzed the highly regioselective conversion of epoxides to halohydrins with elemental halogens

The regioselective ring opening of styrene oxide using elemental iodine and bromine in the presence of disulfides as new catalysts was studied. The conductivity titration and UV spectroscopy were used to study the interaction of iodine with these catalysts. The results indicate that disulfide 11 is efficient in polyiodide formation, and can catalyze this reaction in excellent yield and high reg...

متن کامل

Synthesis and Characterization of γ-Fe2O3@HAp@β-CD Core-Shell Nanoparticles as a Novel Magnetic Nanoreactor and Its Application in the One-Pot Preparation of β-azido Alcohols, β-nitro Alcohols, and β-cyanohydrins

In this study, β-cyclodextrin(β-CD) supported, hydroxyapatite encapsulated γ-Fe2O3 (γ-Fe2O3@HAp@β-CD) was successfully prepared and evaluated as a solid-liquid phase transfer catalyst and also a molecular host system and nanoreactor for the nucleophilic ring-opening of epoxides in water for the preparation of β-azido alcohols, β-nitro alcohols, an...

متن کامل

Enantioselective formation and ring-opening of epoxides catalysed by halohydrin dehalogenases.

Halohydrin dehalogenases catalyse the conversion of vicinal halohydrins into their corresponding epoxides, while releasing halide ions. They can be found in several bacteria that use halogenated alcohols or compounds that are degraded via halohydrins as a carbon source for growth. Biochemical and structural studies have shown that halohydrin dehalogenases are evolutionarily and mechanistically ...

متن کامل

Efficient synthesis of β-hydroxy thiocyanates from epoxides and ammonium thiocyanate using 1,4-bis(triphenylphosphonium)-2-butene dichloride as a new catalyst

1,4-bis(triphenylphosphonium)-2-butene dichloride was developed as a new phase transfer catalyst. This quaternized phosphonium salt catalyzed the regioselective ring opening of epoxides by thiocyanate ion to give β-hydroxy thiocyanates in high yields under mild conditions.

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 11  شماره 

صفحات  -

تاریخ انتشار 2015