Our group recently designed and developed a method of oxypentadienyl cation formation. Upon trapping this intermediate with a variety of different nucleophiles, trends showed selective formation of olefin geometry. We propose this phenomenon is through a Non-Classical Hydrogen Bond (NCHB) interaction via a carbenium C+-H…O stabilized within the putative intermediate. Experimental results and theoretical calculations support the existence of this interaction, showcasing novel functional group reactivity.

Unique non-classical hydrogen bond interactions in 2-oxypentadienyl cations

251st National Meeting (2016)

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