Doubly Vinylogous 4H??Pyrones from Pyrylium Salts and Aryl β??Chlorovinyl Ketones

AT Balaban, M Fahmy, MD Gheorghiu…

Index: Balaban, Alexandru T.; Fahmy, Mahmoud; Gheorghiu, Mircea D.; Wray, Victor Liebigs Annalen der Chemie, 1983 , # 10 p. 1807 - 1817

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Abstract

Abstract Aryl β-chlorovinyl ketones react with the methyl group of 2, 6-di-tert-butyl-4- methylpyrylium perchlorate in the presence of pyridine to yield doubly vinylogous 4H- pyrones 3. Only one configuration and conformation from the eight possible structures appears to be present according to IR, UV-VIS, and NMR data. The mass spectral fragmentation is discussed. Protonation of 3 converts these products into pyrylium salts ...