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Reactivity and Crystal Structure of 10,11-Dihydro-10,11-epoxy-5H-dibenzocycloheptene. A Comparison with cis-Stilbene Oxide

DOI: 10.1039/P29900002147

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 2147 - 2151 (1990)

Update date:2022-08-11

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Authors:

Bellucci, GiuseppeBellucci, Giuseppe

Chiappe, CinziaChiappe, Cinzia

Marioni, F.Marioni, F.

Spagna, RiccardoSpagna, Riccardo

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Article abstract of DOI:10.1039/P29900002147

The kinetics and product distributions for the HClO4 catalysed hydrolysis of 10,11-dihydro-10,11-epoxy-5H-dibenzocycloheptene 1 and of cis-stilbene oxide 6 in tetrahydrofuran-water (8:2), have been investigated by HPLC.The former epoxide gives 9,10-dihydroanthracene-9-carbaldehyde 4 and the trans- and cis-10,11-dihydro-5H-dibenzocycloheptene-10,11-diols 2 and 3, in the ratio 6:6:1. cis-Stilbene oxide reacts with a rate constant ca. ten times lower, giving mostly (+/-)-1,2-diphenylethane-1,2-diol.These differences can be explained by the crystal structure of 1, which shows considerable ring strain due to the enlargement of the bond angles at C(10) and C(11).This structure also suggests an explanation for the much lower rate of the microsomal epoxide hydrolase catalysed hydration of 1 relative to 6.

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