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The Reductive σ Bond Cleavage of Barbaralane and 2,6‐Diphenylbarbaralane
Author(s) -
Trinks Rainer,
Müllen Klaus
Publication year - 1987
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.19871200904
Subject(s) - chemistry , protonation , alkylation , nuclear magnetic resonance spectroscopy , cleavage (geology) , alkali metal , bond cleavage , polymer chemistry , metal , medicinal chemistry , spectroscopy , stereochemistry , catalysis , organic chemistry , ion , geotechnical engineering , fracture (geology) , engineering , physics , quantum mechanics
Barbaralane ( 2 ) and 2,6‐diphenylbarbaralane ( 8 ) are synthesized in a straightforward way. The reductive cleavage of the strained hydrocarbons is achieved with alkali metals. The structure of the metallation products, in particular the bonding in the resulting allyl moieties, is elucidated by 1 H‐ and 13 C‐NMR spectroscopy. The chemical behavior (oxidation, protonation, alkylation) sheds light on the modes of stabilization of the alkali metal derivatives.