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Multichromophoric Systems by Diels–Alder Reaction of Barrelene with o ‐Benzoquinones: Tetracyclo[6.2.2.2 3,6 .0 2,7 ]tetradeca‐9,11,13‐triene‐4,5‐diones
Author(s) -
Behr Jürgen,
Braun Ralf,
Grimme Stefan,
Kummer Matthias,
Martin HansDieter,
Mayer Bernhard,
Rubin Mordecai B.,
Ruck Christoph
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2339::aid-ejoc2339>3.0.co;2-2
Subject(s) - chemistry , diels–alder reaction , medicinal chemistry , computational chemistry , organic chemistry , catalysis
Thermal addition of o ‐benzoquinones to barrelenes (bicyclo[2.2.2]octatrienes) produces tetracyclic trienediones of type 1 . These multichromophoric molecules offer a plethora of photochemical reactions of which the most interesting are (1) rearrangement and bisdecarbonylation of the enedione chromophore and (2) [2π + 2π] intramolecular cycloaddition of the face‐to‐face double bonds. Theoretical methods (semiempirical as well as density functional) were also used to investigate the spin multiplicity diversity of these reactions. The diketone 7 (bicyclo[2.2.2]octa‐5,7‐diene‐2,3‐dione) was investigated using He(I) photoelectron spectroscopy.