77697-47-3Relevant academic research and scientific papers
Deamination Reactions. 35. Decomposition of 5-Norbornene-2-diazonium Ions. Derivatives of Bicyclohept-2-ene
Kirmse, Wolfgang,Knoepfel, Norbert,Loosen, Karin,Siegfried, Rainer,Wroblowsky, Heinz-Juergen
, p. 1187 - 1191 (2007/10/02)
Photolysis of 5-norbornen-2-one tosylhydrazone (4) in aqueous sodium hydroxide afforded 4percent of 3-norpinen-2-ol (3) in addition to 5-norbornen-2-ol (5, 10percent) and nortricyclanol (6, 86percent). 3 arises from 5-norbornene-2endo-diazonium ions (2) as shown by the nitrous acid deamination of the epimeric amines 1 and 7. 3-Norpinen-2-one (12) was isolated by oxidation of the deamination products followed by preparative g.l.c. 3 and 12 were synthesized independently from norpinan-2-one (9) via sulfenylation and sulfoxide pyrolysis.The norbornene -> norpinene rearrangement is slightly enhanced by 1-OCH3.The deamination of 1-methoxy-5-norbornen-2endo-amine (14) produced 10percent of 12, as compared to 5.6percent of 3 from 1.
