
%0 Journal Article
%A Brimble, Margaret A. 
%A Johnston, Andrew 
%A Hambley, Trevor W. 
%A Turner, Peter 
%T Crystal Structures of (3<emph type="3">S</emph>&#42;,4<emph type="3">S</emph>&#42;,5<emph type="3">S</emph>&#42;,6<emph type="3">S</emph>&#42;)-3,4-Epoxy- 1,7-dioxaspiro&#91;5.5&#93;undecan-5-ol, (3<emph type="3">R</emph>&#42;,5<emph type="3">S</emph>&#42;,6<emph type="3">S</emph>&#42;)-1,7- Dioxaspiro&#91;5.5&#93;undecane-3,5-diyl Diacetate and (4<emph type="3">S</emph>&#42;,5<emph type="3">S</emph>&#42;,6<emph type="3">S</emph>&#42;)-1,7-Dioxaspiro&#91;5.5&#93;undecane-4,5-diol
%J Australian Journal of Chemistry
%D 1997/04/01
%V 50
%N 2
%P 123-128
%K 
%R https://doi.org/10.1071/C96186
%U https://www.publish.csiro.au/paper/C96186 
%X The structures of (3S&#42;,4S&#42;,5S&#42;,6S&#42;)-3,4-epoxy-1,7-dioxaspiro&#91;5.5&#93;undecan-5-ol (2), (3R&#42;,5S&#42;,6S&#42;)-1,7- dioxaspiro&#91;5.5&#93;undecane-3,5-diyl diacetate (4) and (4S&#42;,5S&#42;,6S&#42;)-1,7-dioxaspiro&#91;5.5&#93;undecane-4,5-diol (5) have been determined by X-ray crystallography. The unsubstituted tetrahydropyran ring in (2) adopts an axial position with respect to the epoxy-substituted ring and the hydroxy group at C5 is syn to the epoxide group. Intermolecular hydrogen bonding is observed between the C5 hydroxy group and O1. The two six-membered rings in (4) adopt chair conformations and the two acetate groups adopt 1,3-diaxial positions. The C5 hydroxy group in (5) assumes an axial position anti to the C-O bond of the neighbouring ring whilst 4-OH occupies an equatorial position. Intermolecular hydrogen bonding is also observed between 4-OH and 5-OH. Compound (2), C9H14O4, M 186&#183;21, crystallized in the monoclinic space group P 21/c with a 7&#183;867(1), b 12&#183;2060(9), c 9&#183;3676(8) &#197;, b 102&#183;744(8), V 877&#183;4(1) &#197; 3 and No 1163 &#91;I &#62; 2&#183;5s (I)&#93;, R 0&#183;031, Rw 0&#183;035. Compound (4), C13H20O6, M 272&#183;30, crystallized in the triclinic space group P 1 with a 9&#183;902(1), b 11&#183;0024(9), c 6&#183;9183(5)&#197;, a 104&#183;078(8), b 96&#183;769(9), g 101&#183;980(8), V 703&#183;8(1) &#197; 3 , No 1657 &#91;I &#62; 2&#183;5s(I)&#93;, R 0&#183;047, Rw 0&#183;044. Compound (5), C9H16O4, M 188&#183;22, crystallized in the orthorhombic space group Pbca with a 25&#183;504(3), b 8&#183;909(2), c 8&#183;038(2) &#197;, V 1826&#183;4(5) QA 3 , No 1096 &#91;I &#62; 2&#183;5s(I)&#93;, R 0&#183;030, Rw 0&#183;030. 
