105731-53-1Relevant articles and documents
Consecutive and Parallel Rearrangements of 2-Azabicyclooctane Derivatives
Bussmann, Reinhard,Heesing, Albert
, p. 1767 - 1782 (2007/10/02)
Derivatives of both 2-azabicyclooct-5-ene and -octane bearing electronegative substituents on nitrogen show several types of rearrangements: 1) Ring closure to the aziridine derivative 14. 2) Consecutive rearrangement of 14 to 6-azabicyclooctanes 15. 3) Rearrangement to 1-azabicyclooct-2-ene 17 and -oct-6-ene systems 19. 4) Oxygen elimination from O-acylhydroxylamines to the corresponding amides (e.g. 12c -> 13c).We have examined these rearrangements especially with the help of 18O labelled educts and MINDO/3 calculations.They occur mostly via ion pairs of different types.The intermediacy of nitrenium ions was excluded.