Hydration of some bicycle ethynyl alcohols and derivatives

Ramakrishnan, V. T. ; Ramachandran, S. ; Venkataramani, P. S. ; Swaminathan, S. (1967) Hydration of some bicycle ethynyl alcohols and derivatives Tetrahedron, 23 (5). pp. 2453-2459. ISSN 0040-4020

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Related URL: http://dx.doi.org/10.1016/0040-4020(67)80081-4


The epimeric ethynyl alcohols II and III react with mercuric acetate to yield the same acetoxy dione VI, also obtained by hydration of the β-ethynyl-α-acetoxy ketone X. Inversion of configuration occurs, therefore, during the conversion of the α-ethynyl alcohol II to the acetoxy dione VI. If the above reaction is done in the presence of pyridine, the ethynyl alcohol II furnieshes the epoxy intermediate XII which isomerizes readily to either the acetoxy dione VI or its epimer XI, obtained independently. The observed inversion of configuration has been interpreted to involve the epoxy intermediate XII.

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Deposited On:21 Nov 2011 05:11
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