The kinetics of product distributions for the HClO4 catalysed hydrolysis of 10,11-dihydro-10,11-epoxy 5H-dibenzo[a,d]cycloheptene 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-dibenzo[a,d]cycloheptene-10,11-diols, 2 and 3, in the (+/-)-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.
REACTIVITY AND CRYSTAL-STRUCTURE OF 10,11-DIHYDRO-10,11-EPOXY-5H-DIBENZO[A,D]CYCLOHEPTENE - A COMPARISON WITH CIS-STILBENE OXIDE
CHIAPPE, CINZIA;
1990-01-01
Abstract
The kinetics of product distributions for the HClO4 catalysed hydrolysis of 10,11-dihydro-10,11-epoxy 5H-dibenzo[a,d]cycloheptene 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-dibenzo[a,d]cycloheptene-10,11-diols, 2 and 3, in the (+/-)-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
