A study of the reactions of 1,3‐diynes with organo‐cuprates and ‐argentates
- 1 January 1981
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 100 (9) , 337-341
- https://doi.org/10.1002/recl.19811000910
Abstract
1,3‐Diynes HCCCCR′ (1, R′ H or Ph) are converted by cuprates [RCuY]M′ (R alkyl; Y Cl, Br or R; M′ Li, MgCl or MgBr) into a mixture of [HC(CuY)C(R)CCR′]M′ (2) and [RCHC(CuY)CCR′]M′ (3). When R is n‐alkyl, adducts2are the major products; adducts3are preferentially formed when R is a branched alkyl. Organoargentates [RAgY]MgCl (R alkyl, Y Br or R) convert diynes1selectively into [RCHC(AgY)CCR′]MgCl (6). The latter regiospecific reaction has been used to prepare functionally substituted enynes RCHC(E)CCR′ (7: E Br, I, allyl, CO2H) in good yields.Keywords
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