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2001
cyclopropanation reactions
cyclopropanation reactions
O 0138
Tetracyclopropylmethane: A Unique Hydrocarbon with S4 Sym— The crucial step in the synthesis of title compound (IV),
16 - 063 metry.
starting from acrylate (I), is the palladium-catalyzed cyclopropanation of
pentadiene (II) with diazomethane. Hydrogenolysis of product (IV) proceeds
with fourfold selective opening of only the distal bonds to afford the previously unknown tetraisopropylmethane (V). The result of the X-ray structure
analysis displays nearly S4 symmetry for the molecules of (IV). In addition,
computed energies and rotational transition structures are given for compounds
(IV) and (V). — (KOZHUSHKOV, SERGEI I.; KOSTIKOV, RAFAEL R.;
MOLCHANOV, ALEXANDER P.; BOESE, ROLAND; BENET-BUCHHOLZ,
JORDI; SCHREINER, PETER R.; RINDERSPACHER, CHRISTOPHER;
GHIVIRIGA, ION; DE MEIJERE, ARMIN; Angew. Chem., Int. Ed. 40
(2001) 1, 180-183; Inst. Org. Chem., Georg-August-Univ., D-37077 Goettingen,
Germany; EN)
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