38365-55-8Relevant articles and documents
Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis
Chen, Shaomin,Gu, Yanlong,Li, Minghao
, p. 10431 - 10434 (2021/10/12)
Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.
Spectroscopic analysis of the products of the cycloaddition reaction of 1-Aryl-2-chlorocyclopropenes and cyclopentadiene
Ding, Mei-Fang,Lee, Chuan-Chen,Lin, Lian-Chun,Lin, Shaw-Tao
, p. 285 - 289 (2014/05/06)
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. 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. Copyright
Ionic liquids accelerating cycloaddition between 1-aryl-2-halocyclopropenes and furan
Ding, May-Fan,Lin, Shaw-Tao,Chang, Woan-Ju
experimental part, p. 240 - 247 (2010/09/16)
Treatment of a series of 1-aryl-2,2-dihalocyclopropanes with t-BuOK at-10 °C gave the corresponding 1-aryl-2-halocyclopropenes, which react with furan in a RTIL to give a fair good yield of the [4+2]-cycloadducts with more than 90% of the exo-isomer. The imidazolium type ionic liquids are able to accelerate this cycloaddition process with high steric selectivity. Neither pyrrole nor thiophene undergoes the cycloaddition with cyclopropene to form the [4+2]-cycloadduct. 1-Aryl-3,3-difluoro-2-halocyclopropenes are inert towards furan even at a temperature higher than 100 °C.