Synthesis, Chemistry and Structure of Some 1,1-Dimethylcyclopropazulenes

Payne, Alan; Skelton, B.; White, A.; Wege, D.

doi:10.1002/slct.201601168

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Authors

Payne, Alan

Skelton, B.

White, A.

Wege, D.

Date

2016

Type

Journal Article

Metadata

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Citation

Payne, A. and Skelton, B. and White, A. and Wege, D. 2016. Synthesis, Chemistry and Structure of Some 1,1-Dimethylcyclopropazulenes. Chemistry Select. 1 (16): pp. 5339-5346.

Source Title

Chemistry Select

DOI

10.1002/slct.201601168

School

Department of Chemistry

URI

http://hdl.handle.net/20.500.11937/50398

Collection

Curtin Research Publications

Abstract

1,1-Dimethylcycloprop[e]azulene and 1,1-dimethylcyclo-prop[f]azulene derivatives were prepared through a short syn-thesis from thiophene-1,1-dioxides using a Houk-Leaver azu-lene synthesis. The strain caused by the fusion of thecyclopropane ring had no effect on electrophilic aromatic sub-stitution reactions. X-ray structures of these compoundsshowed that cycloprop[e] azulenes have no or very small straininduced bond localisation, whereas cycloprop[f]azulene showssome minor localisation.