Tetrahedron p. 5841 - 5848 (1986)
Update date:2022-08-03
Topics:
Elnagar, H.Y.
Chow, K.H.
Johnson, A.T.
Somanathan, R.
Nunez, P.
et al.
The preparations and silver-assisted acetolyses of the 1-methoxy (5), 1-methyl (6), 1-carbomethoxy (7), and 1-nitro (8) derivatives of trans-7,8-dichlorodibenzobicyclo <2.2.2> octa-2,5-dienes are described.Rearranged products possessing the dibenzobicyclo <3.2.1> octadiene skeleton were identified.With compound 5, the P8:P7 ratio (ratio of products derived from ionizations of C8-Cl and C7-Cl bonds) was 1.3.For 6 and 7, the corresponding P8:P7 ratios were 0.4 and 33 respectively.Acetolysis of 8 led to products in detectable quantities from ionization of the C8-Cl bond only.The data support the proposal by Cristol that the transition states for these solvolytic rearrangements more closely resemble phenonium ion-like intermediates than benzyl cations.
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