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ESR. Spectra and Structures of Radical Anions in the Dibenzo[a, e]cyclooctene Series

✍ Scribed by Fabian Gerson; William B. Martin Jr.; Georges Plattner; Franz Sondheimer; Henry N. C. Wong

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
610 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

ESR. studies are reported for the radical anions of 5,6‐didehydro‐ and 5,6,11,12‐tetradehydro‐dibenzo[a,e]cyclooctene (III and IV, resp.), in addition to that of dibenzo[a,e]cyclooctene (II) itself, the spectrum of which has been reexamined. Comparison of the proton and ^13^C coupling constants for II·⊖, III·⊖ and IV·⊖ indicates that the three radical anions do not differ greatly in their electronic and molecular structures. This statement implies that II·⊖ should also be substantially planar, i.e., the tub‐shaped eight‐membered ring in II is expected to flatten on passing from the neutral molecule to its radical anion. Support for postulating such a change in geometry, analogous to that encountered with the parent cyclooctatetraene (I), is provided by INDO calculations.

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