Controlled [3+2] and [2+2] Cycloadditions of 1,3‐Bifunctional Allenes with C 60  by Using a Flow Reaction System | Zendy

Ueda Mitsuhiro | Zendy; Hayama Miho | Zendy; Hashishita Hiroyuki | Zendy; Munechika Aiko | Zendy; Fukuyama Takahide | Zendy

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Controlled [3+2] and [2+2] Cycloadditions of 1,3‐Bifunctional Allenes with C 60 by Using a Flow Reaction System

Author(s) -

Ueda Mitsuhiro,

Hayama Miho,

Hashishita Hiroyuki,

Munechika Aiko,

Fukuyama Takahide

Publication year - 2019

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201901072

Subject(s) - cycloaddition , chemistry , bifunctional , cyclobutane , cyclopentene , amine gas treating , fullerene , medicinal chemistry , allene , organic chemistry , stereochemistry , catalysis , ring (chemistry)

The reaction of 1,2‐diaryl‐1,2‐diketones, propiolic acid esters, and C 60 in the presence of Et 3 N gave cyclopentene‐annulated fullerenes through a [3+2] cycloaddition. They were formed in two Et 3 N‐promoted steps, namely, the generation of 1,3‐bifunctional allenes and the cycloaddition of 1,3‐bifunctional allenes with C 60 . Interestingly, when a similar reaction was conducted using a flow packed‐bed reactor in combination with a silica‐supported tertiary amine, cyclobutane‐annulated fullerenes were obtained through a [2+2] cycloaddition.

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