108404-72-4Relevant academic research and scientific papers
ACETOLYSES OF 1-SUBSTITUTED TRANS-7,8-DICHLORODIBENZOBICYCLO OCTADIENES.
Elnagar, H.Y.,Chow, K.H.,Johnson, A.T.,Somanathan, R.,Nunez, P.,et al.
, p. 5841 - 5848 (1986)
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 octa-2,5-dienes are described.Rearranged products possessing the dibenzobicyclo 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.
