105815-52-9

Upstream product

• 3693-58-1 2-Azabicyclo<2.2.2>oct-5-en 
• 109638-19-9 3,3-Dimethyl-2-azabicyclo<2.2.2>oct-5-en-hydrochlorid 
• 109638-21-3 2-(Benzoyloxy)-3,3-dimethyl-2-azabicyclo<2.2.2>oct-5-en 
• 109638-20-2 3,3-Dimethyl-2-azabicyclo<2.2.2>oct-5-en-2-oxyl 
• 109638-18-8 3,3-Dimethyl-2-nitroso-2-azabicyclo<2.2.2>oct-5-en 
• 98-59-9 p-toluenesulfonyl chloride 
• 105731-48-4 3,3-Dimethyl-2-azabicyclo<2.2.2>oct-5-en-2-ol 
• 109638-54-2 3,3-Dimethyl-2-aza-bicyclo[2.2.2]oct-5-ene 
• 105731-48-4 3,3-Dimethyl-2-aza-bicyclo[2.2.2]oct-5-en-2-ol 

Downstream Products

• 105731-50-8 4-exo-Chlor-7,7-dimethyl-6-tosyl-8-tosyloxy-6-azabicyclo<3.2.1>octan 

Relevant academic research and scientific papers

Consecutive and Parallel Rearrangements of 2-Azabicyclooctane Derivatives

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.

KONSEKUTIVE UMLAGERUNGEN EINES 2-AZABICYCLOOCTEN-DERIVATES IN DAS 1-AZATRICYCLO2,7>- UND DAS 6-AZABICYCLOOCTAN SYSTEM

In contrast to similar ring systems the O-tosyl derivative 2 is rearranged exclusively to the tricyclic aziridine 4.Further tosylation produces the bicyclic tosyl amide 5.The corresponding O-benzoyl-derivatives 6 rearrange in the usual manner with ?-assis