Synthesis of Imidized Cyclobutene Derivatives by Strain Release of [1.1.1]Propellane
Xiaofan Du, Di Xu, Gongcheng Xu, Chuanming Yu, Xinpeng Jiang
Abstract
Herein, we report the metal-free synthesis of imidized methylene cyclobutane derivatives via a strain-release driven addition reaction of [1.1.1]propellane. Using this strategy, the methylene cyclobutyl cation intermediate generated by protonation of [1.1.1]propellane was found to be trapped by nitriles to form a nitrilium ion intermediate, which subsequently reacted with carboxylic acids to produce imidized methylene cyclobutene derivatives via a Mumm-type rearrangement.
Topics & Concepts
ChemistryCyclobutenePropellaneCyclobutaneMethyleneProtonationStrain (injury)StereochemistryMedicinal chemistryBicyclic moleculeComputational chemistryIonOrganic chemistryRing (chemistry)Internal medicineMedicineSynthesis and Properties of Aromatic CompoundsSynthetic Organic Chemistry MethodsOrganoboron and organosilicon chemistry