SYNTHESIS, REACTIONS, AND STRUCTURAL STUDIES OF 2-CARBON BRIDGED SPIROPENTANES

The syntheses of three 4,5-disubstituted derivatives of tricyclo[4.1.0 .0(1,3)]heptane (3) are reported. The relative stereochemistry of the oxygen substituents in these compounds was deduced by C-13 NMR spectro scopy and unequivocally confirmed by single-crystal X-ray analysis of the thiocarbonate derivative 15, The experimental results obtained fro m reaction of the 2,4-diol 6 under Swern conditions and with TPAP were explained by the results of ab initio calculations at the MP2/6-31G level of theory.