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

✍ Scribed by Balaban, Alexandru T. ;Fahmy, Mahmoud ;Gheorghiu, Mircea D. ;Wray, Victor

Book ID: 102900414
Publisher: John Wiley and Sons
Year: 1983
Tongue: English
Weight: 549 KB
Volume: 1983
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198319831013

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✦ Synopsis

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 4__H__‐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 which may exist in three tautomeric forms. Their structure in solution and in the solid state is discussed.

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