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B IRCH ‐Reduktion von [2.2] Metacyclophan
Author(s) -
Reiner J.,
Jenny W.
Publication year - 1969
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19690520620
Subject(s) - chemistry , singlet state , ring (chemistry) , ammonia , mass spectrum , stereochemistry , nmr spectra database , broad spectrum , nuclear magnetic resonance spectroscopy , metal , crystallography , spectral line , mass spectrometry , organic chemistry , combinatorial chemistry , excited state , astronomy , chromatography , physics , nuclear physics
Metal‐ammonia‐reduction of [2.2] metacyclophan led to 5, 8, 13, 16‐tetrahydro‐[2.2] metacyclophan (II). The structure of this new ring system was confirmed by UV.‐, NMR.‐and mass spectra analyses. The NMR.‐spectrum of II in solution shows an AA ′ BB ′‐system for the ‐CH 2 CH 2 ‐groups. This part of the spectrum is temperature dependant. It collapses and coalesces to a broad singlet at approximately 145°C. A chair‐like conformation and conformational changes of II are discussed.