Cyclodimerization of 3,2-Stevens rearrangement products of 1,9-bisammonium salts containing a 5-oxanonane-2,7-diyne-1,9-diyl group

1,9-Bisdimethylammonium salts containing a 5-oxanonane-2,7-diyne-1,9-diyl along with alkoxycarbonylalkyl group, undergo double 3,2-Stevens rearrangement under the action of corresponding sodium alcoholates to form allene diamino esters whose prototropic isomerization under the action of dilute HCl gives rise to diketo diesters. The latter undergo 1,4-alcohol elimination under the reaction conditions and yield diene keto esters that cyclodimerize into cyclohexene derivatives. The bisammonium salt with a cyanomethyl group rearranges to form an allene dinitrile, which isomerizes into a diene compound.