Cycloaddition reactions of (C6F5)2BN3 with dialkyl acetylenedicarboxylates.

نویسندگان

  • Rebecca L Melen
  • Douglas W Stephan
چکیده

The 1,3-dipolar cycloaddition reactions of the electron deficient boron azide, (C6F5)2BN3 (1) with the electron-poor acetylenes RO2CC≡CCO2R (R = Me, Et) afforded the new mono- and bis-1,2,3-triazole derivatives and .

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

Boron azides in Staudinger oxidations and cycloadditions.

Staudinger reactions of Cy2BN3 with tri-substituted phosphines (R3P) yielded the boron-nitrogen-phosphorus linked systems Cy2BN=PR3 (R = Et, (t)Bu, Cy, Ph) (1a-1d respectively). Similarly, reaction of (C6F5)2BN3 with the phosphines P(t)Bu3, PPh3, Ph2PC≡CPh and Ph2PC≡CPPh2 yielded (C6F5)2BN=PR3 (2a-d respectively). In contrast, the reaction of (C6F5)2BN3 with Ph2P-C≡Cp-tol in the presence of exc...

متن کامل

Synthesis with perfect atom economy: generation of furan derivatives by 1,3-dipolar cycloaddition of acetylenedicarboxylates at cyclooctynes.

Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldehydes to yield polycyclic products 3b-d, orthoesters 4a-c, ketones 5 or epoxides 6a,b, respectively...

متن کامل

A facile route to diastereomeric phosphorus ylides. Chemoselective synthesis of dialkyl (E)-2-[1-(2-oxocyclopentylidene)ethyl]-2-butenedioates.

2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphine and dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-lambda(5)-phosphanylidene)succinates. These compounds undergo intramolecular Wittig reactions in boiling benzene to produce highly strained spirocyclobutene derivatives, which spontaneously undergo ring-opening reactio...

متن کامل

Kinetic study and mechanism investigation of the reactions between triphenylphosphine, dialkyl acetylene dicarboxylates and NH-acid such as Harman

The Kinetic studies were made of the reactions between triphenylphosphine, dialkyl acetylenedicarboxylates in the presence of NH-acid, such as harman. To determine the kinetic parameters of the reactions, they were monitored by UV spectrophotometery. The second order fits were automatically drawn and the values of the second order rate constant (k2) were calculated using standard equations with...

متن کامل

Microwave-Assisted Synthesis of Novel Functionalized Ketenimines and Azadienes via a Solvent-Free Reaction of Isatoic Anhydride, Alkyl-Isocyanides and Dialkyl Acetylenedicarboxylates

Ketenimines and azadienes are transient intermediates in organic chemistry especially in elimination-addition processes and in the formation of heterocyclic systems. These compounds play a considerable role as intermediates in the synthesis of heterocyclic ring systems. In this present research synthesis of novel ketenimines and azadienes via multicomponent reactions (MCRs...

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:
  • Dalton transactions

دوره 44 11  شماره 

صفحات  -

تاریخ انتشار 2015