Metal template reactions. XVII. The attempted dimerization of amino carbonyl compounds containing a supporting donor atom

Abstract

Attempts to effect metal template condensative dimerizations of the amino aldehydes (4), (11) and(12) and the amino ketone (24) have been unsuccessful. Oxidation of the alcohol(9) did not allow isolation of the aldehyde (4). The alcohol (17) underwent oxidation to give crude aldehyde (11),but the latter gave an unidentified mixture of products on attempted reaction with metal ions. The alcohol (20) was stable to oxidation, probably because of hydrogen bonding. The amino aldehyde(12) could not be isolated from the reduction of the nitro aldehyde (22), the product being the alcohol(20). The amino ketone (24) was fully characterized, but proved unreactive in attempted reactions with metal ions, again possibly as a result of strong hydrogen bonding.