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Synthesis, Chemistry and Structure of Some 1,1‐Dimethylcyclopropazulenes
Author(s) -
Payne Alan D.,
Skelton Brian W.,
White Allan H.,
Wege Dieter
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601168
Subject(s) - azulene , chemistry , electrophilic substitution , cyclopropane , electrophilic aromatic substitution , thiophene , electrophile , ring (chemistry) , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry , catalysis
1,1‐Dimethylcycloprop[ e ]azulene and 1,1‐dimethylcycloprop[ f ]azulene derivatives were prepared through a short synthesis from thiophene‐1,1‐dioxides using a Houk‐Leaver azulene synthesis. The strain caused by the fusion of the cyclopropane ring had no effect on electrophilic aromatic substitution reactions. X‐ray structures of these compounds showed that cycloprop[ e ]azulenes have no or very small strain induced bond localisation, whereas cycloprop[ f ]azulene shows some minor localisation.