Polyene acids. Part 11. Preparation of α-tritiated (or deuteriated) conjugated enoic and dienoic acids and their examination by triton magnetic resonance spectroscopy

Autor:	John A. Elvidge, Ramachandra B. Mane, Manouchehr Saljoughian, John R. Jones
Rok vydání:	1978
Předmět:	chemistry.chemical_compound chemistry Decarboxylation Aryl Pyridine Organic chemistry Nuclear magnetic resonance spectroscopy Conjugated system Malonic acid Polyene Ene reaction
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :1191-1194
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19780001191
Popis:	Decarboxylation in boiling pyridine of conjugated ene[OO′-3H]dioic acids (from aryl or alkyl aldehydes and malonic acid, followed by exchange tritiation with labelled water) efficiently provided α-tritiated trans-αβ-unsaturated acids. Extended to croton- and cinnam-aldehydes, the method yielded conjugated dienoic acids labelled at both α- and γ-positions as shown by 3H n.m.r. Labelling at only the α-position was achieved by thermal monodecarboxylation of the intermediate from cinnamaldehyde. Mechanisms are discussed. Similar reactions can be used for the preparation of deuteriated αβ-unsaturated acids.
Databáze:	OpenAIRE
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