Ph. D. THESIS 2009
Ph. D. THESIS 2009
Ph. D. THESIS 2009
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Table 7. The selected molecular parameters of bicyclo[3.3.1]nonane-3,7-dione<br />
calculated by DFT method using B3LYP exchange-correlation function with 6-<br />
31G** basis set.<br />
O1-C3<br />
C3-C4<br />
C4-H4<br />
C4-H5<br />
C4-C5<br />
C5-C9<br />
C5-C6<br />
C3-C2<br />
C9-C1<br />
C9-H12<br />
C4-C3-C2<br />
Coord. B3LYP/6-31G**<br />
Bond lengths (Å)<br />
Angle (Degree)<br />
20<br />
1.2182<br />
1.5252<br />
1.1007<br />
1.0941<br />
1.5467<br />
1.5396<br />
1.5467<br />
1.5252<br />
1.5396<br />
1.0977<br />
116.466<br />
1.6. Attempts of synthesis of bicyclic compounds of spiro-bis(1',5'-dioxane)<br />
type<br />
The synthesis of spiro-1,3-dioxane bicyclic compounds through acetalization<br />
process starting from bicyclo[3.3.1]nonane-3,7-dione dione 2 and different<br />
symmetrically 2,2-substituted 1,3-propanediols was an important step to create<br />
a synthon bearing two functionalized sites, critically required in<br />
macrocyclization reactions.<br />
O O + 2<br />
HO<br />
HO<br />
R 1<br />
R 2<br />
7 R 1, R 2: CH 3<br />
8 R 1, R 2: CH 2Br<br />
1. PTSA, C 6H 6, reflux<br />
2. K10, MW<br />
R 1<br />
R 2<br />
R 1, R 2: CH 3<br />
R 1, R 2: CH 2Br<br />
R 1<br />
R 2