New syntheses for 2-bicyclo(3.3.1)nonanone and 7-bicyclo-(3.3.1)nonen-2-one were developed. The saturated ketone was prepared
from phenol and acrylonitrile via a novel intramolecular
S[subscript N]2 cyclization process. A Friedel-Crafts cyclization of 3-(3-cyclohexenyl)propanoyl chloride permitted synthesis of the unsaturated
ketone from 4-cyclohexene carboxaldehyde. The formation of
the bicyclo(3.3.1)nonane rather than a bicyclo(3.2.2)nonane skeleton...
3-Methyl-2,4-dioxabicyclo [3.3.1] nonane and 7-hydroxy-3-methyl-2, 4-dioxabicyclo [3.3.1] nonane were synthesized by the
method of Croxall, Glavis and Neher, although in low yields.
The structure of both compounds was proven by analytical
methods and analysis of their spectral properties.
Tentative configuration of C-3 in both compounds was
assigned on the assumption...
Bicyclo [6.1.0] non-4-ene was prepared by two routes; (1) reaction
of cis-cis-1, 5-cycloöctadiene with methylene iodide and zinc-copper
couple, (2) sodium-methanol reduction of 9, 9-dibromobicyclo-[6.1.0] non-4-ene. The bicyclononene was characterized by its infrared
spectrum, nuclear magnetic resonance spectrum and common
physical properties. The olefin was hydrogenated to bicyclo [6.1.0] -...