Synthesis Of Dodecahedrane Research Articles

Leo A. Paquette

Leo A. Paquette, 85, died on Jan. 21 in Columbus, Ohio. “Leo was a prolific organic chemist. His research contributions included heterocyclic chemistry, natural products synthesis, and properties of architecturally interesting compounds. I am particularly fond of his combination of domino Diels-Alder reactions and photochemistry to prepare the unsaturated hydrocarbon triquinacene. Leo is best known for the first synthesis of dodecahedrane, which also started with a domino Diels-Alder reaction. Leo was tireless in his service to the chemistry community—for example, on the editorial boards of Organic Syntheses and Organic Reactions.”—David J. Hart, friend and colleague Most recent title: Distinguished University Professor, Ohio State University Education: BS, chemistry, Holy Cross College, 1956; PhD, chemistry, Massachusetts Institute of Technology, 1959 Survivors: Wife, Estelle; son, Ron; daughters, Donna, Linda, Lisa, and Susan To recognize your late loved one or colleague, submit obituary information at ...

Precursors to dodecahedrane.

The title compounds, (2R,2"S,3b'S,4a'R,7b'S,8a'R)-perhydrodispiro[furan-2,3'-dicyclopenta[a,e]pentalene-7',2"-furan]-5,5"-dione, C(20)H(26)O(4), and (3aR,3bR,4aR,4bS,5aS,8aR,8bR,9aR,9bS,10aS)-perhydrodipentaleno[2,1-a:2',1'-e]pentalene-1,6-dione, C(20)H(26)O(2), are intermediates identified during the synthesis of dodecahedrane. Crystallographic studies have established the ring-junction stereochemistry for these important intermediates. All the ring junctions are cis-fused, and the molecular packing is stabilized by van der Waals interactions.

ChemInform Abstract: Synthesis of Triquinacene Derivatives. New Approach Towards the Synthesis of Dodecahedrane.

AbstractSequential treatment of the lactol (I) with ethynylmagnesium bromide (II), tBuMeZSiCI (III) and Me3SiCl (IV) yields a diastereomeric mixture of (V).

An approach to the synthesis of dodecahedrane: the X-ray crystal structures of six intermediate compounds

The X-ray crystal structures (0.03 < R < 0.06) of six compounds isolated during an approach to the synthesis of dodecahedrane are described. The highly substituted C13-tetraquinane (4) and the C19-heptaquinanetrione (6) are twisted out of mirror symmetry to minimise steric interactions. The bridged C19-hexaquinanetriones (7) and (8) and the C19-hexaquinanetriones (9) show signs of strain in the molecular skeleton and the doubly bridged C19-hexaquinanetrione (10) is even distorted showing both bond stretching and bond compression.

Polyhedrane syntheses hotly pursued

The synthesis of dodecahedrane, the last of the classical uniform convex polyhedranes, has been accomplished by organic chemistry professor Leo A. Paquette and his coworkers at Ohio State University, Columbus [ J. Am. Chem. Soc. , 104, 4503 (1982)]. This achievement opens the doors to comparisons of dodecahedrane's actual properties with those calculated for it, and to studies of this and related systems in ways that likely will advance knowledge of the fundamental nature of organic compounds. There also are predictions that substituted dodecahedranes may be useful as drugs. And there is a certain beauty, in that chemists have expressed in hydrocarbon structures the geometrical forms that ancient Greek philosophers related to the basic structure of the universe. The dodecahedrane molecule is a regular 20-carbon polyhedron with 12 pentagonal sides. Paquette made 1,16-dimethyldodecahedrane in late 1980. Of the other hydrocarbons based on Platonic solids, cubane was made by Philip E. Eaton at the University ...

Towards the synthesis of dodecahedrane

Towards the synthesis of dodecahedrane

Towards the synthesis of dodecahedrane II. The crystal and molecular structure of tetrahydro-C16-hexaquinacene-1,9-dione*

Towards the synthesis of dodecahedrane II. The crystal and molecular structure of tetrahydro-C₁₆-hexaquinacene-1,9-dione*