Synthesis, Reactions, and Structural Studies of Two-Carbon Bridged Spiropentanes
The Journal of Organic Chemistry1998Vol. 63(5), pp. 1402–1407
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Abstract
The syntheses of three 4,5-disubstituted derivatives of tricyclo[4.1.0.01,3]heptane (3) are reported. The relative stereochemistry of the oxygen substituents in these compounds was deduced by 13C NMR spectroscopy and unequivocally confirmed by single-crystal X-ray analysis of the thiocarbonate derivative 15. The experimental results obtained from 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.
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