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Scientific article
English

Synthesis of Cycloproparenes via Aromatization of 7-Oxanorbornenes with Low-Valent Titanium

Published inHelvetica Chimica Acta, vol. 72, no. 7, p. 1608-1617
Publication date1989
Abstract

1H-Cyclopropa[b]naphthalene 3c and the 2,7-diphenyl-substituted derivative 3a have been synthesized via cycloaddition of the appropriate isobenzofurans 1a and 1b to 1-bromo-2-chlorocyclopropene and aromatization of the adducts with low-valent Ti. The same procedure afforded the 2,7-dimethyl-H-cyelopropa[g]isoquinoline (15), but failed for the parent azacompound. Reaction of adducts of furans to 1-bromo-2-chlorocyclopropenes with low-valent Ti produced mixtures of cyclopropabenzenes 19 and 1,6-dihalogeno-1,3,5-cycloheptatrienes 18. The latter could be converted to cyclopropabenzenes with BuLi.

Funding
  • Swiss National Science Foundation - 2.602-0.87
Citation (ISO format)
MULLER, Paul, SCHALLER, Jean-Pierre. Synthesis of Cycloproparenes <i>via</i> Aromatization of 7-Oxanorbornenes with Low-Valent Titanium. In: Helvetica Chimica Acta, 1989, vol. 72, n° 7, p. 1608–1617. doi: 10.1002/hlca.19890720721
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ISSN of the journal0018-019X
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