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Tetracyclopropylmethane: A Unique Hydrocarbon with S 4 Symmetry
Author(s) -
Kozhushkov Sergei I.,
Kostikov Rafael R.,
Molchanov Alexander P.,
Boese Roland,
BenetBuchholz Jordi,
Schreiner Peter R.,
Rinderspacher Christopher,
Ghiviriga Ion,
de Meijere Armin
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010105)40:1<180::aid-anie180>3.0.co;2-k
Subject(s) - diazomethane , symmetry (geometry) , yield (engineering) , catalysis , hydrocarbon , chemistry , crystallography , computational chemistry , physics , organic chemistry , mathematics , thermodynamics , geometry
Surprising symmetry, surprising synthesis : Dicyclopropyldiethenylmethane ( 2 ), prepared from dicyclopropylketone ( 1 ) in several steps, was successfully cyclopropanated with a large excess of diazomethane in the presence of palladium( II ) acetate yielding the structurally interesting tetracyclopropylmethane ( 3 ; 92 % yield). Upon catalytic hydrogenation, 3 was quantitatively converted into tetraisopropylmethane ( 4 ). X‐ray structure analysis established S 4 symmetry for 3 and D 2d symmetry for 4 , in excellent agreement with the B3LYP/6‐31+G** computed structures.