Allenes. Part XIV. The synthesis of allenynols and allenenols by the reduction of 4,6-diyn-2-en-1-ols and diynediols with lithium aluminium hydride

Abstract

The reduction of 4,6-diyn-2-en-ols with an excess of lithium aluminium hydride gives allenenes (3,5,6-trien-1-ols) as the main product and allenynes as the minor product. DL-Marasin, claimed to be the product from the reduction of non-2-en-4,6,8-triyn-1-ol, was shown to be a minor component only. Reduction with dialkoxylithium aluminium hydride gave improved yields of allenynes together with allenenes whereas the lithium aluminium hydride–butane-2,3-diol complex gave allenynes only.