Craig R. Smith, D. E. Justice, J. Malpass
1994
Citations
0
Influential Citations
10
Citations
Journal
Tetrahedron
Abstract
Abstract 9-Methyl-9-azabicyclo[4.2.I]nonan-1-ol (homotropan-1-ol; homophysoperuvine) and -non-7-en-1-ol (homotrop-7-en-1-ol) have been synthesised together with the nor- systems and N-benzyl derivatives. The bicyclic amino-alcohols are shown to be in tautomeric equilibrium with the corresponding 4-aminocyclooctanones and -oct-2-enones; similar behaviour is also observed in oxabicyclic analogues. A rearrangement during attempted deprotection of the MEM ether derived from 9-benzyl-9-azabicyclo-[4.2.1]nonan-1-ol yielded N-benzyl-10-azabicyclo[3.3.2]dec-3-en-2-one. An attempt to introduce a 4-azido-substituent into a protected cyclooct-3-enone gave, instead, a novel tetracyclic triazoline.