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Stereochemie der Denitrogenierung von optisch aktivem 9,10‐Dihydro‐5,6‐diazalumibullvalen zu optisch aktivem 3,4‐Dihydrosemibullvalen
Author(s) -
Askani Rainer,
Andermann Thomas,
Müller Karl Michael
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250821
Subject(s) - chemistry , optically active , diradical , derivative (finance) , cyclopentene , medicinal chemistry , thermal decomposition , stereochemistry , organic chemistry , singlet state , catalysis , atomic physics , physics , financial economics , economics , excited state
Stereochemical Course of the Denitrogenation of Optically Active 9,10‐Dihydro‐5,6‐diazalumibullvalene to Optically Active 3,4‐Dihydrosemibullvalene Thermal decomposition of optical active diazalumibullvalene derivative (+)‐ 6 gives optical active dihydrosemibullvalene (+)‐ 5 . The absolute configurations of optical active 6 and 5 were determined by correlation to tricyclooctanone 9 and 2‐cyclopentene‐1‐acetic acid ( 21 ), respectively. From these results it is concluded that thermal denitrogenation of 6 occurs by concerted six‐electron cycloreversion competing most likely to a multi‐step N 2 elimination via the symmetrical diradical intermediates 8 and 7 .