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

An Improved Synthesis, Molecular-Structure, and Properties of 1,4-Dihydro-Dicyclopropa[b,g]naphthalene

B Halton, R Boese, D Blaser and Q Lu

Australian Journal of Chemistry 44(2) 265 - 276
Published: 1991

Abstract

A marked improvement in the preparation of 1,4-dihydrodicyclopropa[ b,g ]naphthalene (4) from isotetralin (7) has been achieved by selecting conditions which avoid the unwanted olefin (12). The easily available dicycloproparene (4) has C2h symmetry in the crystal lattice with the space group P21/n. The geometry is readily rationalized by the concept of 'bent bonds' that are also suggested by X-X difference electron density maps. Cheletropic biaddition of dichlorocarbene to (4) provides the dicyclobutanaphthalenes (15) and (16). Attempted Petersen olefination to mono- and di-alkylidene derivatives, e.g. (21) and (22), is foiled by a reluctance of (4) to provide an easily interceptible anion.

https://doi.org/10.1071/CH9910265

© CSIRO 1991

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