Abstract
Tricyclo[3.3.0.03,7]octane-2,4-dione (2,4-stelladione, 3), tricyclo[3.3.0.03,7]octane-2,6-dione (2,6-stelladione, 4), and 2-oxotricyclo[3.3.0.03,7]octane-6-thione (5) were synthesized. Key steps in the procedures were a Paterno-Buchi reaction followed by an oxetane splitting with a strong base. Structure analysis on single crystals of 4 and 5 revealed long central C−C bonds (1.59 A) of the stellane skeleton. The He(I) photoelectron spectra of 3, 5, and 4-methylenetricyclo-[3.3.0.03,7]octan-2-one (9) were recorded and interpreted on the basis of quantum-mechanical calculations (HF-SCF, 6-31G* basis). The large energy difference between the first PE bands of 3 (0.8 eV) is due to a strong interaction between the lone pairs on the oxygen atoms and the σ frame.
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