Frustrated Alternative Approaches towards the Synthesis of a Thermally Stable 1,2-Diazacyclobutene.

ABSTRACT: We have previously demonstrated that an appropriately substituted four-membered-ring 1,2-diazacyclobutene is a useful compound in organic synthesis for the introduction of strained 1,2-diazetidine rings. In order to further explore the reactivity of this interesting heterocycle, we sought a method to improve upon the poor synthetic yield reported earlier. A novel route involving the synthesis of a similarly substituted 1,2-diazetidine compound followed by free-radical bromination and base-catalyzed debromination appeared promising. While there are some studies on the synthesis of the desired 1,2-diazetidine precursor, when we attempted its synthesis, we instead observed the exclusive formation of an eight-membered "dimer"-like compound. The structure of this compound was confirmed via sing

SUBMITTER: Breton GW 

PROVIDER: S-EPMC11397526 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature