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Second‐Ring Diels‐Alder Adducts of Substituted Pentacenes
Author(s) -
Jia Zhiying,
Nakajima Kiyohiko,
Kanno Kenichiro,
Song Zhiyi,
Takahashi Tamotsu
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800376
Subject(s) - aromatization , adduct , diels–alder reaction , steric effects , pentacene , ring (chemistry) , chemistry , chloranil , selectivity , medicinal chemistry , stereochemistry , organic chemistry , catalysis , layer (electronics) , thin film transistor
Substituted pentacene derivatives, 1,4,6,13‐tetrabutyl‐2,3‐bis(methoxycarbonyl)pentacene 1 and 1,2,3,4,6,8,9,10,11,13‐decapropylpentacene 2 , occurred Diels‐Alder reaction with most dienophiles at the central‐ring. The second ring adduct was obtained only in the case of TCNE or chloranil probably due to the steric hindrance of such dienophiles. On the other hand, reaction of substituted dihydropentacene derivatives with dienophiles was followed by aromatization gave second‐ring adducts in perfect selectivity.