The Reaction of Ketene with Pyridine1

The chemistry of Wollenberg's yellow adduct of pyridine with ketene is elucidated by degradative studies. The sub- stance is a pyronodihydroquinolizon...
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THEREACTION OF KETENEWITH PYRIDINE

April 20, 1956 [CONTRIBUTION FROM THE

DEPARTMENT OF CHEMISTRY,

1625

UNIVERSITY O F SOUTHERN CALIFORNIA]

The Reaction of Ketene with Pyridine1 BY JEROME A, BERSONAND WILLIAMM. JONES RECEIVED AUGUST22, 1956 The chemistry of Wollenberg’s yellow adduct of pyridine with ketene is elucidated by degradative studies. The substance is a pyronodihydroquinolizone. It disproportionates to a colorless dihydro derivative and a yellow, strongly fluorescent dehydro derivative. The mode of union of the ketene residues follows the “head-to-tail” rule.

As part of his classical survey2 of the chemistry of the ketenes, Staudinger investigated the action of these substances on organic heterocycles. With pyridine and quinoline, ketoketenes formed adducts resulting from attack on the C=N bond of the heterocycle : e.g., pyridine and diphenylketene gave I.3 These substances were inordinately un-

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