sented implies that I-R is antihomoaromatic, i.e., that it is less stable than the isomeric radical II-R in which the conjugated system is not cyclic. Extension of the available orbital argument to the anions suggests that II-Ris preferred to I-R-, but experimental confirmation is lacking.Breslow10 has demonstrated the utility of electrochemical methods in obtaining otherwise unavailable information on very unstable antiaromatic species, such as triphenylcyclopropenyl anion. We suggest that this method is even more valuable in the study of antihomoaromatic species because these may be generated by electron-transfer reactions of the corresponding homoaromatic species, before they revert to the more stable linearly conjugated isomer. Attempts to prepare antihomoaromatic species by chemical reactions such as protonation11 should yield preferentially the linearly conjugated species and not the desired intermediate.(8) If the isomerization of I-R+ to II-R+ precedes electron transfer to II-R+, then the reduction potential reflects the free-energy changes for the isomerization and the electron transfer, as in the reduction of cyclooctatetraene to its planar radical anion: T.
Bicyclo[3.1.0]hex-3-en-2-yl Cation1 Sir:Recently developed synthetic procedures2 for specific introduction of deuterium at the 2-and 6-endo positions of the parent bicyclo[3.1.0]hex-3-en-2-yl cation 1 make possible the study of the properties of this species by nuclear magnetic resonance (nmr) spectroscopy of Fellow, 1967Fellow, -1970 (5-FG1-GM-38,024-02).
Die Photooxidation des Diens (I) in Methanol bei ‐78°C ergibt das Dioxetan (ID, das beim Erwärmen in Tetrachlorkohlenstoff den Aldehyd (III) und Aceton ergibt.
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