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1,7‐Dioxa[7](2,7)pyrenophane: The Pyrene Moiety Is More Bent than That of C 70
Author(s) -
Bodwell Graham J.,
Bridson John N.,
Houghton Tom J.,
Kennedy Jason W. J.,
Mannion Michael R.
Publication year - 1999
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/(sici)1521-3765(19990604)5:6<1823::aid-chem1823>3.0.co;2-i
Subject(s) - moiety , pyrene , isomerization , dehydrogenation , chemistry , valence (chemistry) , photochemistry , anthracene , bent molecular geometry , stereochemistry , organic chemistry , catalysis
The most distorted pyrene moiety yet prepared (see picture) has been synthesized by the valence isomerization of a tethered [2.2]metacyclophane‐1,9‐diene to a 10b,10c‐dihydropyrene and in situ dehydrogenation by 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) at 80 °C. The end‐to‐end bend of the pyrene moiety exceeds that of the corresponding part of the equator of D 5h C 70 .