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RESEARCH ARTICLE

Previous Contents Vol 63(4)

Synthesis of Diyne Substituted 2-Hydroxy Acids, Esters, and Amides

Florian H. M. Graichen ^A ^B , Andrew C. Warden ^A , Stella Kyi ^A and Michael S. O’Shea ^A

+ Author Affiliations

- Author Affiliations

^A CSIRO, Division of Molecular and Health Technologies, Bag 10, Clayton South, Vic. 3800, Australia.

^B Corresponding author. Email: florian.graichen@csiro.au

Australian Journal of Chemistry 63(4) 719-722 https://doi.org/10.1071/CH09639
Submitted: 9 December 2009 Accepted: 9 February 2010 Published: 8 April 2010

Abstract

A series of diyne substituted 2-hydroxy acids and derivatives have been prepared and characterized. Alkylation of butane-2,3-diacetal protected glycolic acid with haloalkyl substituted diyne compounds gave the corresponding diacetal protected diyne substituted 2-hydroxy acids. Diacetal deprotection through acid mediated hydrolysis, transesterification, or aminolysis afforded the 2-hydroxy-diyne acid, ester, or amide derivatives, respectively. A novel class of polydiacetylenes was produced through topochemical polymerization of a 2-hydroxy diyne acid and compared with the polymerization of non-hydroxylated diyne acids.

Acknowledgement

We thank the GRDC (Grains Research and Development Corporation), Australia for financial support and Drs Jack Ryan and Peter Duggan for critical comments on the manuscript.

References

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[46] The conversions into the halides were carried out under very mild conditions, which had no impact on the sensitive diyne functionality.

[47] After 15 min the reaction mixture was warmed to –50°C to –40°C, prior to addition of the halo-diyne compounds. The excess of base did not lead to dialkylation of 16 and had no impact on the sensitive diyne functionality of our electrophiles. The slightly increased temperature was necessary to avoid the precipitation of the halides in the reaction mixture at –78°C.