Home > Iowa Academy of Science > Journals & Newsletters > Proceedings of the Iowa Academy of Science > Volume 61 (1954) > Annual Issue
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
©1954 Iowa Academy of Science, Inc.
Language
en
File Format
application/pdf
Recommended Citation
Shriner, R. L. and Schaeffer, R. E.
(1954)
"Synthesis of 4-Piperidinoflavan,"
Proceedings of the Iowa Academy of Science, 61(1), 269-270.
Available at:
https://scholarworks.uni.edu/pias/vol61/iss1/32