Synthesis of aryl and heterocyclic acetylenes via copper acetylides
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 16,p. 2173-2176
- https://doi.org/10.1039/j39690002173
Abstract
Ethynylbenzene (I), 1-ethynylnaphthalene (IX), 2-ethynylthiophen (IV), and 2-ethynyl-5-iodothiophen (XII) have been prepared from the corresponding iodo-derivatives (V), (VII), (II), and (X), by reaction with copper(I) 3,3-diethoxyprop-1-ynide to give αβ-acetylenic aldehydes, followed by base-catalysed deformylation. Alternatively, copper(I) 3-tetrahydropyranyloxy-prop-1-ynide gave the αβ-acetylenic alcohols (XVIII), (XIX), (XIII), (XX), and (XV), which were oxidised with nickel peroxide and then deformylated, or oxidised in aqueous alkali directly, to the same acetylenes (I), (IX), (IV), (XII), and 5-ethynyl-2,2′-bithienyl (XVII). The application of this sequence to the protection of terminal ethynyl groups is indicated.Keywords
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