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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 , organic chemistry , stereochemistry , photochemistry , 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.