Abstract: The highly strained cyclopropabenzynes 13 and 15 have been generated by use of the complex base system of tert-butoxide ion/amide ion, commencing with 2-and 3- bromocyclopropabenzene. Benzynes 13 and 15 have been trapped as the furan adducts 14 and 16, respectively. Fully optimized geometries of 13 and 15, their relative energies, and the strain and electronic properties, as well as the regioselectivity of addition of 13, have ...