ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Heterocyclic 12-π- and 14-π-Systems, 34. - Experiments on the Reactivity of 2-Phenyl-5H-naphtho[1,8-bc]furan-5-one (Oxapseudophenalenone)Reactions of 2-phenyl-5H-naphtho[1,8-bc]furan-5-one (1) with perchloric acid in alcohols yield the 4-alkoxy-8-hydroxy-1-naphthyl phenyl ketones 3a-3c which are also obtained from 4,8-dihydroxy-1-naphthyl phenyl ketone (2) in acidic alcoholic solutions. Diphenylketene, naphthylphenylketene, tert-butylcyanoketene, cyanomethylketene, cyanophenylketene react with 1 to give the 2-phenyl-oxapseudophenafulvenes 4-8; thermolysis of 2,5-diazido-3,6-dioxo-1,4-cyclohexadiene-1,4-dicarbonitrile (9) yields in situ the dicyanoketene (10) which reacts with the ketone 1 via elimination of CO2 to give the (2-phenyl-oxapseudophenafulven-5-ylidene)malonodinitrile 11. Compound 11 was not obtained by another route.
Notes:
Die Reaktionen von 2-Phenyl-5H-naphtho[1,8-bc]furan-5-on (1) mit Perchlorsäure in Alkoholen führen zu den (4-Alkoxy-8-hydroxy-1-naphthyl)(phenyl)ketonen 3a-3c, die auch aus (4,8-Dihydroxy-1-naphthyl)(phenyl)keton (2) in sauren alkoholischen Lösungen zugänglich sind. Mit Diphenylketen, Naphthylphenylketen, tert-Butylcyanketen, Cyanmethylketen, Cyanphenylketen werden die 2-Phenyl-oxapseudophenafulvene 4-8 erhalten, mit dem durch Thermolyse von 2,5-Diazido-3,6-dioxo-1,4-cyclohexadien-1,4-dicarbonitril (9) in situ erzeugten Dicyanketen (10) wird unter Eliminierung von CO2 das auf anderen Wegen nicht zugängliche (2-Phenyl-oxapseudophenafulven-5-yliden)malonodinitril 11 synthetisiert.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197919790706
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