Issue 0, 1972

2H-naphtho[1,8-bc]furan and 8-hydroxy-1-naphthaldehyde

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).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 699-704

2H-naphtho[1,8-bc]furan and 8-hydroxy-1-naphthaldehyde

D. Berry and D. C. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1972, 699 DOI: 10.1039/P19720000699

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