π-Extended Alkylidenecycloproparenes

Brian Halton; Mark J. Cooney

doi:10.1071/CH05330

RESEARCH ARTICLE

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π-Extended Alkylidenecycloproparenes

Brian Halton ^A ^B and Mark J. Cooney ^A

+ Author Affiliations

- Author Affiliations

^A School of Chemical & Physical Sciences, Victoria University of Wellington, Wellington, New Zealand.

^B Corresponding author. Email: brian.halton@vuw.ac.nz

Australian Journal of Chemistry 59(2) 118-122 https://doi.org/10.1071/CH05330
Submitted: 12 December 2005 Accepted: 13 January 2006 Published: 7 March 2006

Abstract

Reaction of benzene-1,4-dicarboxaldehyde with anion 6 derived from 1,1-bis(trimethylsilyl)cyclopropa[b]naphthalene 1 gives 4-(methylidene-1H-cyclopropanaphthalenyl)benzaldehyde 7 as a minor product and 1,4-bis(methylidene-1H-cyclopropanaphthalenyl)benzene 8 as the major product of the reaction. With 4-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}benzaldehyde 14, this same anion affords the stilbene-substituted π-extended (1-arylmethylidene)cyclopropanaphthalene 15 as a sparingly soluble orange-red powder.

Acknowledgements

Financial support from the former Victoria University Fellowships Committee (to M.J.C.) and Internal Grants Committee (to B.H.) is gratefully acknowledged. We thank Dr H. Wong of the former DSIR Chemistry Division for recording the 300/75 MHz NMR spectra and Mr. B. Clarke of Canterbury University for collecting the accurate mass data.

References

^* As cited in Table 2 (Entry 27) of ref. [2].

^† Extinction coefficients were not determined as 1.40 mg of 8 did not dissolve completely in 250 mL of solvent.

^‡ The limited solubility precluded quantitative measurements.

π-Extended Alkylidenecycloproparenes

Abstract

Acknowledgements

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