Ontology highlight
ABSTRACT:
SUBMITTER: Sterling AJ
PROVIDER: S-EPMC8159217 | biostudies-literature | 2020 Apr
REPOSITORIES: biostudies-literature
Chemical science 20200413 19
[1.1.1]Propellane is the ubiquitous precursor to bicyclo[1.1.1]pentanes (BCPs), motifs of high value in pharmaceutical and materials research. The classical Lewis representation of this molecule places an inter-bridgehead C-C bond along its central axis; 'strain relief'-driven cleavage of this bond is commonly thought to enable reactions with nucleophiles, radicals and electrophiles. We propose that this broad reactivity profile instead derives from σ-π-delocalization of electron density in [1.1 ...[more]