Ph. D. research topic of Franz-Manfred Schüngel 

at the Universität Göttingen

August 1996 - December 1999



    Acepentalene (C10H6) is a highly strained, antiaromatic hydrocarbon.  Although the idea of synthesizing it by intro- ducing  two  additional  double  bonds into the triquinacene  (C10H10)  molecule was already published in the 60's by Woodward along with his triquinacene synthesis,[1] it consistently slipped through the hands of more[2] or less[3] skilled chemists  like  a  wet  soap  in  the  shower. After more than 30 years at least the existence of acepentalene could be proven,[4] but a (matrix) isolation of the compound is still elusive.[5]  My results on the topic were somewhat diminished by the fact that I did not work on the field of expensive useless polymers. 
 
Literature and remarks:
 
[1]   R. B. Woodward, T. Fukunaga, R. C. Kelly, J. Am. Chem. Soc. 1964, 86, 3162. 
[2]   I will not give any names here. 
[3]   And here even less! 
[4]   R. Haag, D. Schröder, T. Zywietz, H. Jiao, H. Schwarz, P. v. R. Schleyer, A. de Meijere, 
       Angew. Chem. 1996, 108, 1413; Angew. Chem. Int. Ed. Engl. 1996, 35, 1317. 
[5]   Elusive means: No literature yet!
 
If you are interested in the topic check my publications:
 
R. Haag, F.-M. Schüngel, B. Ohlhorst, T. Lendvai, H. Butenschön, T. Clark, M. Noltemeyer, T. Haumann, 
     R. Boese, A. de Meijere, Chem. Eur. J. 1998, 4, 1192-1200. 
A. de Meijere, R. Haag, F.-M. Schüngel, S. I. Kozhushkov, I. Emme, Pure Appl. Chem. 1999, 71, 253-264. 
A. de Meijere, F. Gerson, P. Merstetter, P. R. Schreiner, F.-M. Schüngel, J. Chem. Soc. Chem. Commun. 1999,
    2189-2190.
Better still, buy my thesis (I get some money from it):
 
It is extremely scientific, nicely written in decent german and has a nice cover picture of the north sea on the front cover. Due to its rareness it is a sought-after collectors item. It is compatible to a mindboggingly range of bookshelfs and fully recyclable. 

Franz-Manfred Schüngel 
Auf dem Wege zum Acepentalen: Das Radikal-Anion 
ISBN 3-89712-830-6

 
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(c) 1999 by Franz-Manfred Schüngel