SYNTHETIC APPROACHES TO NORTROPANES AND NORTROP-6-ENES - INTRAMOLECULAR DISPLACEMENT BY NITROGEN IN 7-MEMBERED RINGS

A NAYLOR, N HOWARTH, J R MALPASS

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Abstract

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.

Original languageEnglish
Pages (from-to)451-468
Number of pages18
JournalTetrahedron
Volume49
Issue number2
Publication statusPublished - 8 Jan 1993

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