283-58-9Relevant academic research and scientific papers
Reductive cleavage of Propellane-type Hydrazinium Dications as a Route to Medium-sized Ring Bicyclic Diamines with Bridgehead Nitrogen Atoms
Alder, Roger W.,Sessions, Richard B.,Bennet, Andrew J.,Moss, Richard E.
, p. 603 - 610 (2007/10/02)
Procedures are described for the preparation of 1,5-diazoniatricyclodecane (9), 1,5-diazoniatricycloundecane (10), 1,6-diazoniatricyclododecane (11), 1,6-diazoniatricyclotridecane (12), and 1,6-diazoniatricyclotetradecane (13) salts by the alkylation of 1,5-diazabicyclooctane and 1,6-diazabicyclodecane with suitable difunctional molecules XmY.The central N-N bond of these propellane-type hydrazinium dications may be cleaved by a variety of reducing agents to yield the bicyclic diamines 1,5-diazabicyclodecane (21), 1,5-diazabicycloundecane (22), 1,6-diazabicyclo-dodecane (23), 1,6-diazabicyclotridecane (24), and 1,6-diazabicyclotetradecane (25).The scope and limitations of this synthetic route to medium-sized ring bicyclic diamines are discussed.
