The chemistry of polyenic and polyacetlenic compounds

Abstract

1. The reactions of sodiomalonic ester with the primary vinylacetylenic bromides formed in the allyl isomerization of tertiary isopropenylacetylenic alcohols have been studied. 2. The reactions of the bromides from 1-bromo-3,4-dimethylpent-4-en-1-yn-3-ol, 2,3-dimethylundec-1-en-4,6-diyne-3-ol, and 2,3-dimethyltridec-1-ene-4,6,8-triyne-3-ol lead to the intramolecular nucleophilic addition of the elements of the malonic ester to the acetylenic bonds with the formation of the corresponding cyclopentene derivatives, the structure of which was confirmed by their IR spectra and some chemical reactions. 3. In the case of the reaction of the bromide from 2,3-dimethylnon-1-en-4-yn-3-ol, no C-C cyclization takes place and, consequently, this intramolecular cyclization depends not only on a cis- configuration of the double bond but also on the electronic nature of the triple bond.