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Synthese von Tricyclo[4.4.1.1 3, 8 ]dodecan‐4, 9‐dion und Tricyclo[4.4.1.1 3, 8 ]dodeca‐4, 9‐dien
Author(s) -
Gerlach H.
Publication year - 1972
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.19720550828
Subject(s) - chemistry , dodecane , medicinal chemistry , sodium hydride , tributyltin hydride , nmr spectra database , hydride , stereochemistry , organic chemistry , spectral line , hydrogen , physics , astronomy
Treatment of 2, 6‐bis‐aminomethyladamantane‐2, 6‐diol (II) with nitrous acid gives tricyclo[4.4.1.1 3, 8 ]dodecane‐4, 9‐dione (III), which is converted into the tricyclo[4.4.1.1 3, 8 ]dodeca‐4, 9‐diene (V) by reduction to the corresponding diols (IV, R = H) and pyrolysis of their O‐4‐methylphenyl thiocarbonate O‐esters. II is accessible from 2, 6‐adamantanedione by reaction with diethyl aluminium cyanide and subsequent reduction with lithiumaluminium hydride. The physical properties of the new compounds including 13 C NMR. spectra of III, V and tricyclo‐[4.4.1.1 3, 8 ]dodecane are given.