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Synthesis of Annulenes via Multiple Wittig Reactions; In‐Situ Dimerization of 1,2;5,6‐Dibenzocyclooctatetraene
Author(s) -
Bornhöft Jan,
Siegwarth Jan,
Näther Christian,
Herges Rainer
Publication year - 2008
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/ejoc.200701174
Subject(s) - annulene , chemistry , wittig reaction , dimer , nuclear magnetic resonance spectroscopy , stereochemistry , diffraction , spectroscopy , in situ , organic chemistry , physics , optics , quantum mechanics
A simple synthetic route to tetrabenzo[16]‐ and hexabenzo[24]annulene systems using one‐pot multiple Wittig reactions is presented. We report the characterization of the all‐ trans ‐isomer of tetrabenzo[16]annulene by NMR spectroscopy and X‐ray diffraction. Several isomers of an unexpected, tetrabenzocyclooctatetraene dimer product are also isolated and identified by NMR‐ and X‐ray diffraction studies.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)