146309-11-7Relevant articles and documents
Synthetic Approaches to Nortropanes and Nortrop-6-enes; Intramolecular Displacement by Nitrogen in 7-Membered Rings
Naylor, Antoinette,Howarth, Nicola,Malpass, John R.
, p. 451 - 468 (2007/10/02)
The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described.The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation.Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described.Nitrogen inversion data for selected nortropane derivatives are included. Key Words: nortropanes/enes; 1,4-disubstitute cyclohexanes, cycloheptanes, cyclooctanes and -enes; intramolecular cyclisation; slow nitrogen inversion.
