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The Relative Reactivities of the Isomeric Methyl Pyridinecarboxylates in the Acylation of Certain Ketones. The Synthesis of β-Diketones Containing Pyridine Rings

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/ja01156a035· OSTI ID:4420401
 [1];  [1]
  1. Univ. of Pittsburgh, PA (United States)

Using sodium methoxide to effect the condensations, the relative reactivities of the three methyl pyridinecarboxylates and methyl benzoate in the Claisen acylation of acetone, acetophenone and pinacolone have been found to be methyl pico-linate > isonicotinate > nicotinate and/or benzoate. An explanation for this order of reactivity is given and certain comments on the factors influencing the Claisen acylation of methyl ketones are made.

Research Organization:
Univ. of Pittsburgh, PA (United States)
Sponsoring Organization:
US Atomic Energy Commission (AEC)
NSA Number:
NSA-05-005151
OSTI ID:
4420401
Report Number(s):
NYO--939
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 12 Vol. 73; ISSN 0002-7863
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English