2H-naphtho[1,8-bc]furan and 8-hydroxy-1-naphthaldehyde
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 699-704
- https://doi.org/10.1039/p19720000699
Abstract
Syntheses of 2H-naphtho[1,8-bc]furan (1) are described. It is C-protonated, as are its nitrogen analogues, forming a stable salt; and it is oxidised by air to 8-hydroxy-1-naphthaldehyde. Solvent shifts in the spectra of this aldehyde and related compounds are interpreted in terms of conformational changes caused by hydrogen bonding. Naphthofuran (1) is oxidised by lead tetra-acetate; one of the four products isolated is a dialdehyde (21) structurally similar to gossypol (22).Keywords
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