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Adamantan als Baustein neuer Araliphane Synthese, Spektroskopie und Kristallstrukturen
Author(s) -
Dohm Joachim,
Vögtle Fritz,
Nieger Martin,
Rissanen Kari
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240436
Subject(s) - chemistry , adamantane , moiety , benzene , molecule , crystal structure , crystallography , stereochemistry , meso compound , enantiomer , nuclear magnetic resonance spectroscopy , solid state , organic chemistry
Adamantane as a Building Block of New Araliphanes – Synthesis, Spectroscopy, and Crystal Structures Exchange of benzene units for aliphatic building blocks in cyclophanes leads to new molecules of the “araliphane” type. With adamantane the araliphanes 2 – 4 are synthesized. Their stereochemical behavior as shown by NMR studies and X‐ray crystallographic analyses differs significantly from that of their aromatic counterparts. The signals of the intraannular adamantane hydrogens are strongly shifted upfield up to δ=– 2.18 (in 2 ). 4 is obtained as a racemic mixture of enantiomers (in the crystalline state) and shows a boat‐like deformation of the benzene moiety.