ChemInform Abstract: Consecutive and Parallel Rearrangements of 2‐Azabicyclo(2.2.2)octane Derivatives.

Abstract

ChemInform Abstract The hydroxylamine (III) is prepared from the nitrosamine (I). Tosylation of (III) results in ring closure to give the aziridines (V), which on further tosylation undergo consecutive rearrangement to the azabicyclo(3.2.1)octanes (VI). On heating in toluene, the aroyloxy derivatives (VIII) undergo rearrangement to the azabicyclo(3.2.1)oct-6-ene systems (IX) or oxygen elimination to the amides (X). Similar studies are described for some derivatives of the saturated 2-azabicyclo(2.2.2)octane system. The rearrangements are examined with the help of 18O labelled educts and MINDO/3 calculations.