ChemInform Abstract: An Approach Toward Isoindolobenzazepines Using the Ammonium Ylide/Stevens [1,2]‐Rearrangement Sequence.

Abstract

An Approach Toward Isoindolobenzazepines Using the Ammonium Ylide/Stevens [1,2]-Rearrangement Sequence.-Treatment of the diazo amides (I) and (IV) with Rh 2 (O-Ac) 4 results in formation of isoindolobenzazepines via ammonium ylide generation and subsequent Stevens [1,2]-rearrangement. Additionally, it is shown that the diazo amines (VI) also undergo this ammonium ylide/rearrangement sequence, but the analogues (VIII) do it not. Starting from (VIII) formation of ammonium ylides does not occur but generation of isobenzofuran intermediates which can be trapped with DMAD.