Abstract A synthesis of 2H-1-benzoxocin from readily available compounds was accomplished. The potentially 'aromatic'π-excessive systems 2H-1-benzoxocinyl and 6H- dibenz [b, f] oxocinyl anions were generated from their corresponding conjugate acid precursors 7c and 8, respectively. It was found that 2H-1-benzoxocinide 3d lacks the type of π-frame stability associated with the parent 2H-oxocinide 1d and that the dibenzo analog ...