Science of Synthesis

Chataigner, I.; Harrison-Marchand, A.; Maddaluno, J., Science of Synthesis, (2005) 26, 1184.

The hydration of a triple bond under the catalytic action of mercury(II) or other metallic salts[‌517‌] is widely used for terminal acetylenic compounds. Because this reaction follows Markovnikov's rule, only ketones are obtained and not aldehydes. The hydration of internal alkynes is encountered less frequently for the synthesis of oxo esters. The problem of its regiochemistry is summarized in Section ‌26.10.1.1.7.1‌ and so is not presented here. Typical cases of cyclic 3-oxo esters ‌175‌[‌518‌] and 4-oxo esters ‌177‌[‌519‌] (from alkyne ‌176‌) are illustrated in ‌Scheme 106‌.

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References