2988-70-7Relevant academic research and scientific papers
Deamination Reactions, 37. Decomposition of Bicyclononane- and Bicyclonon-2-ene-9-diazonium Ions
Kirmse, Wolfgang,Hellwig, Georg
, p. 2744 - 2754 (2007/10/02)
Bicyclononane-exo-9-diazonium ions (9) have been generated from the corresponding nitrosourea (8) and base.In weakly alkaline solution (E)-3-methoxycyclononene (11) was formed by disrotatory ring opening of (9).In the presence of sodium methoxide 1,2-cyclononadiene (13) and exo-9-methoxybicyclononane (15) were additional products, presumably arising via carbene 12.Bicyclonon-2-ene-exo-9-diazonium ions (21) decomposed without participation of the double bond to give the (Z,E)-methoxycyclononadienes 22 and 23.The 21-derived carbene 29 afforded the bicyclic ether 30 and the elusive 1,2,4-cyclononatriene (32).In contrast to its lower homologs, 29 did not undergo a carbene-carbene rearrangement (29 -> 31).
