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Propellanes of the Glycoluril Series and Bridged Tetrazocines
Author(s) -
Gompper Rudolf,
Nöth Heinrich,
Rattay Wilfried,
Schwarzensteiner MarieLuise,
Spes Peter,
Wagner HansUlrich
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198710391
Subject(s) - antiaromaticity , chemistry , propellane , alkylation , deprotonation , urea , condensation , heteroatom , medicinal chemistry , bicyclic molecule , organic chemistry , ring (chemistry) , molecule , aromaticity , ion , catalysis , physics , thermodynamics
The dianions 1 may be regarded as bishomo‐antiaromatic 12π‐electron systems. They are formed by reduction of 2,6‐bridged 1,3,5,7‐tetrazocines 2 with potassium in liquid NH 3 or by deprotonation of the propellane 3 with KO t Bu. Compounds 2 and 3 can be easily synthesized by condensation of cyclic 1,2‐diketones and urea followed by Meerwein alkylation. Tetraazasemibullvalenes are not formed.