476364-39-3Relevant academic research and scientific papers
Thermal and hyperbaric addition of N,N- and N,O-binucleophiles on cycloalkylidenic bromo esters
Rulev, Alexandre Y.,Maddaluno, Jacques
, p. 590 - 598 (2007/10/03)
The thermal and high-pressure (11 kbar) induced reaction between 2-bromo-2-(cycloalkylidene)acetates and N,O- and N,N-binucleophiles (such as ethylenediamines or aminoethanols) provides morpholin-2-ones and piperazin-2-ones. Thus, in contrast to simple primary amines, binucleophiles do not form spirocyclic derivatives. The expected Michael addition competes with a cascade reaction consisting of a migration of the double bond followed by the substitution of the newly established allylic halogen and a lactonization (lactamization), and eventually ended by a back-migration of the double bond. Copyright
