SYNTHESIS AND TAUTOMERISM OF 9-AZABICYCLO[4.2.1]NONAN-1-OLS (NORHOMOTROPAN-1-OLS), N-ALKYL AND 7,8-DEHYDRO- DERIVATIVES, AND OXABICYCLIC ANALOGS

9-Methyl-9-azabicyclo[4.2.1]nonan-1-ol (homotropan-1-ol; homophysoperu vine) and -non-7-en-1-ol (homotrop-7-en-1-ol) have been synthesised to gether with the nor-systems and N-benzyl derivatives. The bicyclic ami no-alcohols are shown to be in tautomeric equilibrium with the corresp onding 4-aminocylooctanones and -oct-2-enones; similar behaviour is al so observed in oxabicylic 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 a ttempt to introduce a 4-azideo-substituent into a protected cyclooct-3 -enone gave, instead, a novel tetracyclic triazoline.