Intriguing Electrophilic Reactivity of Donor-Acceptor Cyclopropanes: Experimental and Theoretical Studies

Maxime Dousset (1) , Jean-Luc Parrain (1) , Gaëlle Chouraqui (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

A new reactivity of donor–acceptor cyclopropanes (DACs) has been highlighted and, for the first time, we report that they could formally behave as nucleophiles and be func-tionalized at their C3 position. The donor–acceptor cyclo-propane acts as a formal nucleophilic synthetic equivalent of a 1,2-zwitterion and could be described as an umpolung synthon.

Mots clés: reaction mechanisms; zwitterions; cyclopropanes; Donor-acceptor systems; density functional calculations

Domaines: Chimie organique; Chimie théorique et/ou physique

Maxime Dousset, Jean-Luc Parrain, Gaëlle Chouraqui. Intriguing Electrophilic Reactivity of Donor-Acceptor Cyclopropanes: Experimental and Theoretical Studies. European Journal of Organic Chemistry, 2017, pp.5238-5245. ⟨10.1002/ejoc.201701058⟩. ⟨hal-01687389⟩