The kinetics, products, and stereochemistry of the polar addition of hydrogen chloride, bromide, and iodide to a series of substituted propiolic and phenylpropiolic acids have been studied. An analysis of the structure–reactivity and structure–stereochemistry relations is related to a major stereospecific process for trans-addition and a minor, cis-addition process.
K. Bowden and M. J. Price, J. Chem. Soc. B, 1970, 1472 DOI: 10.1039/J29700001472
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