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Transanular Interactions in Difunctional Medium Rings, 5. Spectroscopic Investigations of Bicyclic Boraamines
Author(s) -
Wiesmann Reinhard F.,
Rademacher Paul
Publication year - 1994
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.19941270620
Subject(s) - bicyclic molecule , chemistry , intramolecular force , substituent , boranes , alkyl , nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , organic chemistry , boron
The endo ‐7‐[(dialkylamino)methyl]‐3‐borabicyclo[3.3.1]nonanes 1 and 2 have been synthesized and their intramolecular complex formation of the corresponding 2‐azonia‐1‐boratatricyclo[4.3.1.1 4,8 ]undecanes 3 and 4 has been studied in the gas phase by UV photoelectron spectroscopy and in solution by 11 ‐NMR spectroscopy. Deviations of the characteristic spectral features from those of the monofunctional bicyclic boranes 5 and amines 6 and 7 indicate that in the gas phase the (dimethylamino)boranes with a B ‐alkyl substituent adopt the tricyclic form 3a–c whereas the diethylamino and the B ‐methoxy derivatives 1e and 2 prefer the bicyclic structure. In solution some deviations from this behavior are observed.