Abstract:
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 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.

KeyWords Plus:
<1.1.1>PROPELLANE, CHEMISTRY

Addresses:
Wiberg KB, Yale Univ, Dept Chem, 225 Prospect St, New Haven, CT 06520 USA.
Yale Univ, Dept Chem, New Haven, CT 06520 USA.

Publisher:
AMER CHEMICAL SOC, WASHINGTON

IDS Number:
ZC310

ISSN:
0022-3263