Mechanism of formation and stabilities of the new dioxadiazadecalin systems. Ring-chain tautomerism

A. Star, B. Fuchs

Research output: Contribution to journalArticlepeer-review

Abstract

A linear free energy relationship study is presented for the reactions of threo- and erythro-1,4-diamino- and -2,3-diaminobutanediols (1, 2) with six p-substituted benzaldehydes, the end products of which are the novel cis- and trans-1,5-dioxa-3,7-diazadecalin (DODAD, 7ci, 7tr) and -1,5-diaza-3,7- dioxadecalin (DADOD, 8ci, 8tr) systems. The consecutive double 1,3-oxazane ring closures take place mostly via Schiff bases and are moderately polar ring-chain tautomeric reactions with low positive p-values (0.69) affected by steric strain, stereoelectronic effects, and intramolecular hydrogen bonds. These are relatively slow processes, which may occur in the solid as well, but are greatly enhanced by acid catalysis.

Original languageEnglish
Pages (from-to)1166-1172
Number of pages7
JournalJournal of Organic Chemistry
Volume64
Issue number4
DOIs
StatePublished - 19 Feb 1999

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