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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Studies in the Cycloproparene Series: Formation of a New Dimer of 1H-Cyclopropa[b]naphthalene

Brian Halton, Carissa S. Jones, Peter T. Northcote and Roland Boese

Australian Journal of Chemistry 52(4) 285 - 290
Published: 1999

Abstract

1-(Trimethylsilyl)-1H-cyclopropa[b]naphthalene (10) and its 1-methyl derivative (11) have been isolated as pure compounds from use of a lipophilic size exclusion gel. Acylation of the 1H-cyclopropa[b]naphthalenyl anion (2) is effected with N,N -dimethyl-benzamide and -acetamide to give (5) and (6), respectively. Analogous reactions with the 1-(trimethylsilyl)-1H-cyclopropa[b]naphthalenyl anion (9) do not yield the 1-acyl-1-(trimethylsilyl)-1H-cyclopropa[b]naphthalenes (12) and (13); instead the novel 6-methyl- 7H-dibenzo[b,g]fluorene (15) results from attempted acetylation. Compound (15), a formal dimer of 1H-cyclopropa[b]naphthalene (1), is formed also from anion (9) both in toluene and from addition of hydrocarbon (1); its structure is assigned from spectroscopic data and confirmed by single-crystal X-ray analysis.

https://doi.org/10.1071/C98179

© CSIRO 1999

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