Synthesis, Chemistry and Structure of Some 1, 1‐Dimethylcyclopropazulenes. Issue 16 (11th October 2016)

• Record Type: Journal Article
• Authors: Payne, Alan D.; Skelton, Brian W.; White, Allan H.; Wege, Dieter
• Is Part Of: ChemistrySelect. Volume 1:Issue 16(2016)
• Page Start: 5339
• Page End: 5346
• Publication Date: 2016-10-11
• Subjects: Azulene -- Cycloproparene -- Photochemistry -- Strain induced bond localisation (SIBL) -- Thiophene-1, 1-dioxide; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201601168
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: 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. Abstract : 1, 1‐Dimethylcycloprop[ e ]azulenes and 1, 1‐dimethylcycloprop[ f ]azulene 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.