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

Topics:

Authors:

Bellucci, Giuseppe

Chiappe, Cinzia

Marioni, F.

Spagna, Riccardo

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

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.

Full text of DOI:10.1039/P29900002147

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:2-Phenylacetophenone

Cas No:451-40-1

R&D Labs maybe for 451-40-1

Taizhou Crene Biotechnology co.ltd

Contact:86-576-88813233 88205808

Address:Economic Developed Zone of Taizhou Zhejiang China
Zhengzhou Minzhong Pharmaceutical Co.,ltd

Contact:0086-371-65797115

Address:15/F,Jiangshan Bldg, NO.126 Huanghe Road,Zhengzhou, China
JIEJIE GROUP CO.,LTD.

Contact:+86 021-51698675

Address:1701, Jielong Plaza, No.618 Pingliang Rd, ShangHai,China
Brichem ( Haikou ) Co. Ltd.

Contact:86-898-65311214

Address:Room 102, BLDG. 68 Jiangnan City, No. 66 Heping Road,Haikou, Hainan, China
Jiaozuo Zhongwen Trading Coporation Limited

Contact:+86 0391-3553810

Address:East Renmin Road

Relevant to this article

Correlation between structural studies and third order NLO properties of selected new quinolinium semi-organic compounds

Doi:10.1016/j.chemphys.2010.07.007
(2010)
A ONE-FLASK MULTICOMPONENT ANNULATION REACTION AS THE KEY STEP IN A TOTAL SYNTHESIS OF SPIROBICYCLIC (+/-)-β-VETIVONE

Doi:10.1016/S0040-4020(01)81566-0
(1992)
Morphological evolution in zinc electrodeposition

Doi:10.1149/1.2096949
(1989)
Benzimidazolyl based Schiff base palladium complex in an ionic liquid: an effective combination for Suzuki coupling

Doi:10.1080/00958972.2017.1311412
(2017)
Doi:10.1016/S0277-5387(00)80623-3
(1989)
Doi:10.1021/jo01284a062
(1967)

Article Doi