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Synthesis and Structures of Trifluoromethyl‐, Fluoro‐, and Azido‐Substituted Hexabenzylhexaazaisowurtzitanes and Isolation of a Novel Hexaazaisowurtzitane‐Based Polycycle
Author(s) -
Klapötke Thomas M.,
Krumm Burkhard,
Piotrowski Holger,
Polborn Kurt,
Holl Gerhard
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390077
Subject(s) - trifluoromethyl , substituent , benzene , chemistry , azide , ring (chemistry) , fluorine , stereochemistry , medicinal chemistry , crystallography , organic chemistry , alkyl
The first hexabenzylhexaazaisowurtzitane cage compounds with trifluoromethyl and azide groups, as well as those with fluorine atoms in the 3‐ and 4‐positions, have been prepared and fully characterized. A study of the substituent influence on the benzene ring regarding the formation of the hexaazaisowurtzitane polycycle in either the 2‐ or 4‐position with CF 3 , F, and N 3 revealed an interesting difference. In all cases with CF 3 , F, and N 3 substituents in the 4‐position, the corresponding hexabenzylhexaazaisowurtzitanes were isolated. The corresponding hexabenzylhexaazaisowurtzitanes were also formed when these substituents were in the 2‐position; however, in addition with azide in 2‐position a novel type of polycycle was isolated and identified. 15 N NMR data and crystal structures of hexabenzylhexaazaisowurtzitane derivatives were obtained and are discussed in detail.