Products of mercuric salt addition to dis ubstituted acetylenes

Nesmeyanov, A. N.; Borisov, A. E.; Savel'eva, I. S.; Osipova, M. A.

doi:10.1007/bf01118745

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1982

1985

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Cited by 3 publications

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“…exclusively anti adducts 37,46,47. Diphenylacetylene affords both syn and anti addition compounds, but in this case the former predominates 43,45,46,…”

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confidence: 99%

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Mercury in organic chemistry. 24. Mercuration and subsequent carbonylation of 4-hydroxy-2-alkyn-1-ones: a novel route to furans

Larock¹,

Liu²

1983

J. Org. Chem.

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Mercuric chloride readily adds to the carbon-carbon triple bond of certain 4-hydroxy-2-alkyn-l-ones (3a, 3b, and 3e) to give vinylmercurials which appear to be the first syn addition compounds of mercuric chloride. These vinylmercurials readily dehydrate to 3-furylmercurials. Palladium-promoted carbonylation of these compounds affords 3-furyl carbonyl compounds.Mercury(II) salts are known to readily add to a variety of acetylenes to afford vinylmercurials (eq 1). Thus, Cl, OAc, SON mercuric halides are reported to add to acetylene (anti),2"7 propyne (anti),8 cyclooctyne,® vinylacetylene (anti?),8•10 11"12

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“…exclusively anti adducts 37,46,47. Diphenylacetylene affords both syn and anti addition compounds, but in this case the former predominates 43,45,46,…”

mentioning

confidence: 99%

“…Terminal alkynes generally give dialkynylmercurials. [36][37][38] Simple internal aliphatic acetylenes appear to afford both regio-and stereochemical mixtures of vinylmercurials with anti adducts predominating,39-42 as illustrated by the reaction of 2-butyne (eq 4), [43][44][45]…”

mentioning

confidence: 99%