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- Title
Heterocyclic Spiro-naphthalenones. Part II. Synthesis and reactions of some spiro [tetrahydrofuran-2,1′-(2′ H-naphthalene)]-2′,5-diones and Spiro [tetrahydrofuran-2,2′-(1′ H-naphthalene)]-1′,5-diones.
- Authors
Berney, Daniel; Schuh, Karlheinz
- Abstract
The spiro-lactone 3 was obtained by N-bromosuccinimide (NBS) oxidation of the carboxylate 2 at − 20°. When 2 was oxidized at 10° the spiro-lactone 4 was the main product. Compound 4 was rearranged with triethylamine to the spiro-lactone 9 whereas the stereoisomeric spiro-lactones 14 and 15 were obtained by NBS oxidation of the carboxylate 13. The ketones 3, 4, 9, 14 and 15 were reduced with NaBH4 to the corresponding alcohols 5, 6, 10, 16 and 18 respectively; these were hydrogenated to the alcohols 7, 8, 11 and 20. The allylic alcohols 5 and 6 gave the benzochromanone 1 when heated in polyphosphoric acid whereas the benzochromanones 12 and 21 were obtained from the alcohols 10 and 16 respectively.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 4, p1399
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610423