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Document Type

Research

Abstract

A study of the reaction of flavylium perchlorate with piperidine showed that piperidine perchlorate was formed plus two other compounds. One of these appears to be 4-piperidinoflavene which should be reducible to 4-piperidinoflavan. This compound had not been described previously, hence its synthesis was undertaken. Flavanone was prepared according to the method of Kostanecki (1). Catalytic reduction of flavanone with hydrogen and a platinum catalyst gave a 79% yield of a compound melting at 145- 147°. This corresponds to the, B-isomer of 4-hydroxyflavan originally obtained by Karrar, Yen and Reichstein (2) as the result of a titanous chloride reduction of flavanone. Mozingo and Adkins (3) also obtained this ,B-isomer by catalytic reduction of flavanone but used copper-chromium oxide at 120° and hydrogen at 100-200 atm. Treatment of the 4-hydroxyflavan with phosphorus tribromide at 0° gave a 52% yield of 4-bromoflavan. An ether solution of this bromo-compound reacted with two equivalents of piperidine to form piperidinium hydrobromide and {3-4 piperidinoflavan. Upon recrystallization from ether, colorless needles were obtained melting at 137-138° which had the correct analysis for this compound.

Publication Date

1954

Journal Title

Proceedings of the Iowa Academy of Science

Volume

61

Issue

1

First Page

269

Last Page

270

Copyright

© Copyright 1954 by the Iowa Academy of Science, Inc.

Language

EN

File Format

application/pdf

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