71413-12-2Relevant academic research and scientific papers
Synthesis, X-Ray structural analysis, and conformational study of anti-[3.3]metacyclophane quinhydrone dimethyl ether
Shinmyozu, Teruo,Hirakawa, Takafumi,Wen, Gang,Osada, Satoshi,Takemura, Hiroyuki,Sako, Katsuya,Rudzinski, Jerzy M.
, p. 205 - 210 (2007/10/03)
Synthesis and X-ray structural analysis of anti-[3.3]metacyclophane-2,11-dione quinhydrone dimethyl ether (3) are described. The formation of anti-3 starting from syn-9 may be ascribed to the syn→anti isomerization of the syn-quinhydrone 17 according to a
Electron Donor-Acceptor Compounds, XX: Intramolecular Quinhydrones of the Metacyclophane Series: Synthesis, Stability, and Charge Transfer Absorptions of Stereoisomeric Metacyclophane Quinhydrones
Staab, Heinz A.,Herz, Claus P.,Doehling, Annelie,Krieger, Claus
, p. 241 - 254 (2007/10/02)
On the attempt to synthesize the syn- and anti-metacyclophane quinhydrones 1 and 2 by demethylation of 3 and 4, resp., and subsequent oxidation the same (2,6)-p-benzoquinonophane (5) was obtained which on catalytic hydrogenation yielded syn-metacyclophane quinhydrone 1.Partial demethylation, however, and following oxidation led from 3 to the dimethyl ether 7 of the syn-quinhydrone 1, and analogously from 4 to the dimethyl ether 8 of anti-metacyclophane quinhydrone 2.The structural assignment of the stereoisomers was confirmed by an X-ray structure analysis of 7.In addition to 7 and 8, the corresponding monomethyl ethers 10 and 12 were obtained. - The anti-metacyclophanes 8 and 12 undergo a complete thermal rearrangement to the syn-isomers 7 and 11, resp., from which a stronger ground state stabilisation by charge transfer interaction is concluded for the donor-acceptor systems of the syn-series. - The quinhydrones 7, 8, 10, 11, and 12 show broad, intensive charge transfer absorptions in the range from 300 to 550 nm which for the pairs of stereoisomers 7/8 and 11/12, in spite of the very different donor-acceptor orientation, are surprisingly similar; the absorption intensity of the CT band, however, is considerably stronger for the anti-quinhydrones than for their syn-isomers.
Electron Donor-Acceptor Compounds, XIX: Intramolecular Quinhydrones of the Metacyclophane Series: syn- and anti-6,9,15,18-Tetramethoxymetacyclophanes as Precursors
Staab, Heinz A.,Herz, Claus P.,Doehling, Annelie
, p. 233 - 240 (2007/10/02)
In the context of the synthesis of metacyclophane quinhydrones (e. g. 1 and 2) the stereoisomeric 7,10,17,20-tetramethoxy-2,13-dithiametacyclophanes (5/6) were synthesized via 8-12.From the disulfones, prepared by oxidation of 5/6, by vacuum gas
