The synthesis of spiro[4.4]nonane-1,6-diols via the catalytic as well as stoichiometric hydrogenation of spiro[4.4]nonane-1,6-dione was studied. Profound effects of the hydrogenation catalysts and reagents on the stereoselectivity of the products were observed. The choice of solvent also was found to have a significant influence on the product selectivity. The opening of a spiro-ring in the starting material was identified as a major side reaction in alcohol solvents. The absolute configuration of the trans, trans-diol was unambiguously determined by X-ray crystallography.

中文翻译：

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通过螺[4.4]壬烷-1,6-二酮的氢化合成螺[4.4]壬烷-1,6-二元醇：氢化剂的深刻作用

研究了螺[4.4]壬烷-1,6-二酮的催化加氢和化学计量加氢合成螺[4.4]壬烷-1,6-二醇。观察到氢化催化剂和试剂对产物的立体选择性的深远影响。还发现溶剂的选择对产物的选择性有很大的影响。原料中的螺环的开口被确定为醇溶剂中的主要副反应。反式，反式-二醇的绝对构型通过X射线晶体学确定。