Ionic liquids accelerating cycloaddition between 1-aryl-2-halocyclopropenes and furan

Ding, May-Fan; Lin, Shaw‐Tao; Chang, Woan-Ju

doi:10.3998/ark.5550190.0011.219

Cited by 3 publications

(1 citation statement)

References 9 publications

(8 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Unsubstituted cyclopropene has explosion liability, while the substituted ones are stable. 71 Consequent to the extra stability of cyclopropene accrued from a halo substituent, it can act as a dienophile. Room temperature ionic liquids (RTIL) are a class of solvents that provide an excellent solubility range compared to commonly existing solvents.…”

Section: Reductive Dehalogenationmentioning

confidence: 99%

Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

et al. 2015

View full text Add to dashboard Cite

gem-Dihalocyclopropanes have wide-spread applications in organic synthesis due to their versatile chemistry. They can serve as substrates for a large range of useful materials such as natural products, alkaloids, cyclopropanes, heterocycles, aromatic ring systems etc. Normally the dihalocyclopropanes are prepared by the addition of dihalocarbene to alkene, but due to the great synthetic efficacy of gem-dihalocyclopropanes a number of methods have been developed for their synthesis. Generally gem-dihalocyclopropanes exist as strained cyclic systems with astonishing kinetic stability. They are capable of undergoing transformations leading to a variety of products which have potential applications in various synthetic organic chemistry fields.

show abstract

Section: Reductive Dehalogenationmentioning

confidence: 99%

Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

et al. 2015

View full text Add to dashboard Cite

show abstract

Spectroscopic Analysis of the Products of the Cycloaddition Reaction of 1‐Aryl‐2‐chlorocyclopropenes and Cyclopentadiene

Ding

Lee

Lin

et al. 2013

J Chinese Chemical Soc

Self Cite

View full text Add to dashboard Cite

The treatment of a series of 1-aryl-2,2-dihalocyclopropanes with t-BuOK at -10°C produces the corresponding 1-aryl-2-halocyclopropenes, which react with cyclopentadiene to produce fairly good yield of [4+2]-cycloaddition products with more than 90% of the endo-isomer. The higher yield obtained from hexane medium then from methanol and ionic liquid demonstrates that the reaction is a nonpolar process.

show abstract

Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement

Gopi

Namboothiri

2013

J. Org. Chem.

View full text Add to dashboard Cite

A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported.

show abstract

Ionic liquids accelerating cycloaddition between 1-aryl-2-halocyclopropenes and furan

Cited by 3 publications

References 9 publications

Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

Spectroscopic Analysis of the Products of the Cycloaddition Reaction of 1‐Aryl‐2‐chlorocyclopropenes and Cyclopentadiene

Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement

Contact Info

Product

Resources

About