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Configuration, Conformation, and Dynamics of Octalene
Author(s) -
Oth Jean F. M.,
Müllen Klaus,
Runzheimer HansVolker,
Mues Peter,
Vogel Emanuel
Publication year - 1977
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197708721
Subject(s) - cyclooctatetraene , annulene , chemistry , adduct , double bond , crystal structure , crystallography , nmr spectra database , crystal (programming language) , spectral line , stereochemistry , computational chemistry , chemical physics , molecule , physics , organic chemistry , astronomy , computer science , programming language
The synthesis, structure, and properties of octalene are described for the first time. This [8]annuleno[8]annulene, accessible in many steps from a tetrahydronaphthalene, is a lemon yellow hydrocarbon that is very air‐sensitive. Independent structural proof was obtained by crystal structure analysis of a triazolinedione adduct. Examination of the 13 C‐NMR spectra at +120, +25, and −150°C ruled out the form with a central double bond and the aromatic form. The temperature dependence of the spectrum indicates mutually independent inversions of the cyclooctatetraene and the cyclooctatriene fragments. The peripheral π‐bonds undergo shifts above about 80°C. The transition state is planar.