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- W1999104787 abstract "Epoxidation and dihydroxylation of the olefin moiety of 2-substituted dibenzobicyclo[2.2.2] octatrienes were investigated. These reactions exhibited substituent effect : 2-nitodibenzo bicyclo[2.2.2]octatriene gave predominantly the syn-epoxide and the syn-diol, with a diastereomeric excess of 54% to 76%. respectively. On the other hand, the 2-methoxy substrate showed only a small preference in the reactions, giving a slight excess of the antiproducts. This effect can be interpreted in terms of the perturbation of the occupied π orbital of the ethylene moiety arising from the mixing of the π orbitals (in particular, the HOMO) of convex-substituted dihydroxyanthracene, wherein the σ type overlaps are involved in a manner similar to the longicyclic conjugation." @default.
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- W1999104787 date "1992-01-01" @default.
- W1999104787 modified "2023-09-27" @default.
- W1999104787 title "Orbital distortion in dibenzobicyclo(2.2.2)octatrienes. Biased epoxidation and dihydroxylation of the olefin moiety." @default.
- W1999104787 cites W1495226765 @default.
- W1999104787 doi "https://doi.org/10.1248/cpb.40.3349" @default.
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