TY - JOUR
T1 - 2-azatricyclo[2.2.1.01,6]heptane
T2 - Synthesis and conversion to 2-azabicyclo[2.2.1]heptanes
AU - Portoghese, P. S.
AU - Sepp, D. T.
PY - 1973
Y1 - 1973
N2 - A facile route to 6-substituted 2-azabicyclo[2.2.1]heptanes via the novel tricyclic system, 2-azatricyclo[2.2.1.01,6]heptane (2), is described. The key intermediate (2) was prepared by oxidation of 4-aminomethylcyclopentene with lead tetra-acetate, and the bicyclic system was obtained by reaction of acetate with 2.MeI. Equilibration of exo- and endo-6-hydroxy-1-methyl-2-azabicyclo[2.2.1]heptane afforded an exo-endo isomeric ratio close to that of norborneol, and on this basis it is suggested that the steric requirements of the nitrogen lone pair are similar to that of CH.
AB - A facile route to 6-substituted 2-azabicyclo[2.2.1]heptanes via the novel tricyclic system, 2-azatricyclo[2.2.1.01,6]heptane (2), is described. The key intermediate (2) was prepared by oxidation of 4-aminomethylcyclopentene with lead tetra-acetate, and the bicyclic system was obtained by reaction of acetate with 2.MeI. Equilibration of exo- and endo-6-hydroxy-1-methyl-2-azabicyclo[2.2.1]heptane afforded an exo-endo isomeric ratio close to that of norborneol, and on this basis it is suggested that the steric requirements of the nitrogen lone pair are similar to that of CH.
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U2 - 10.1016/S0040-4020(01)93346-0
DO - 10.1016/S0040-4020(01)93346-0
M3 - Article
AN - SCOPUS:0015833531
SN - 0040-4020
VL - 29
SP - 2253
EP - 2256
JO - Tetrahedron
JF - Tetrahedron
IS - 15
ER -