Collect. Czech. Chem. Commun. 1982, 47, 858-876

Preparation of 7-oxabicyclo[4.3.0]nonanes and 2-oxabicyclo[4.4.0]decanes specifically labelled with deuterium

František Tureček

Jaroslav Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 121 38 Prague


trans-Annulated 7-oxabicyclo[4,3,0]nonanes, labelled with deuterium at C(1), C(6), C(8) and C(9), and cis-annulated isomers labelled at C(1) and C(6) were prepared by cyclization of the corresponding labelled 2-(2-hydroxyethyl)-cyclohexanols. cis- Annulated 7-oxabicyclo[4,3,0]nonanes labelled at C(5), C(8) and C(9) were prepared by oxymercuration-reduction of labelled 2-(3-cyclohexenyl)ethanols. 2-Oxabicyclo[4.4.0]decanes labelled at C(1), C(3) and C(6) were prepared by cyclization of the corresponding 2-(3-hydroxypropyl)cyclohexanols. cis-Annulated 2-oxabicyclo[4,4,0]decanes labelled at C(4), C(5) and C(10)were obtained by oxymercuration-reduction of 3-(3-cyclohexenyl)-propanols. Conformation of the cis-annulated isomers is discussed.