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Organics, Volume 4, Issue 1
March 2023 - 10 articles
Cover Story: The reaction of the highly electrophilic azo compound MeTAD with bicycloalkadienes via the homo-Diels–Alder reaction provides rapid access to strained heterocycles. These heterocycles serve as precursors to strained azo compounds of both synthetic and theoretical interest. Earlier work by others demonstrated that reaction of MeTAD with unsubstituted, and singly substituted, bicycloalkadienes takes place successfully. However, reaction with 1,2-disubstituted bicycloalkadienes had not yet been explored. Our work demonstrates that disubstitution with the mild electron-withdrawing carboethoxy group permits continued Diels–Alder reactivity, but disubstitution with the very strong electron-withdrawing cyano group prevents reactivity. View this paper
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Organics - ISSN 2673-401X