Benzannulenones. Synthesis of 22,23,24,25-tetradehydrodibenzo[a,g]cycloheneicosen-11-one
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 13,p. 1548-1551
- https://doi.org/10.1039/p19770001548
Abstract
The conjugated ω-(o-ethynylphenyl)alka-dienal (6) and -trienal (7) were prepared and converted by aldol condensations into acyclic ketones, required as potential precursors of tetradehydrodibenzannulenones. Only the bis(ethynylphenyl)tridecahexaenone (1d) afforded the corresponding annulenone, 22,23,24,25-tetradehydrodibenzo[a,g]cycloheneicosen-11-one (2d). The 1H n.m.r. spectrum showed that (2d) is an atropic molecule.Keywords
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