Polyene acids. Part 11. Preparation of α-tritiated (or deuteriated) conjugated enoic and dienoic acids and their examination by triton magnetic resonance spectroscopy
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1191-1194
- https://doi.org/10.1039/p19780001191
Abstract
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.Keywords
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