Heptacyclo(5.5.1.14,10.02,6.03,11.05,9.08,12)tetradecane-13,14- bis(spiro-1 prime-cyclopentane): A New C22H28 Nonacyclic Cage Hydrocarbon. Improved Synthesis Bicyclo(2.2.1)hepta-2,5-diene-7-spiro-1 prime-cyclo-pentane

摘要

An improved, five step synthesis of bicyclo(2.2.1) 2.2.1hepta-2, 5-diene-7-spiro-1'-cyclopentane (1) which affords this material in 15% overall yield (starting with cyclopentadiene) has been developed. Thermal reaction of 1 with iron pentacarbonyl results in cyclodimerization of 1, thereby affording heptacyclo 5.5.1.1(4,10).0(2,6).-O3,11.O(5.9).O(8,12)tetradecane (3) in 41% yield. Compound 3 is a dendroasymmetric molecule with a perpendobiplanar structure belonging to point group D2d. (Author)