DIMETHYL O[4.2.2.0(2,5)]DECA-3,7,9-TRIENE-7,8-DICARBOXYLATE (COOKSONSDIESTER) REVISITED - COPE REARRANGEMENT AND EPOXIDATION SITE SELECTIVITY

Authors
WARRENER RN ELSEY GM PITT IG TIEKINK ERT RUSSELL RA
Citation
Rn. Warrener et al., DIMETHYL O[4.2.2.0(2,5)]DECA-3,7,9-TRIENE-7,8-DICARBOXYLATE (COOKSONSDIESTER) REVISITED - COPE REARRANGEMENT AND EPOXIDATION SITE SELECTIVITY, Tetrahedron letters, 35(7), 1994, pp. 1075-1078
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
7
Year of publication
1994
Pages
1075 - 1078
Database
ISI
SICI code
0040-4039(1994)35:7<1075:DO(>2.0.ZU;2-O
Abstract
Dimethyl o[4.2.2.0(2,5)]deca-3,7,9-triene-7,8-dicarboxylate (Cookson's diester) (8) is rearranged thermally via a double Cope reaction to it s ring-degenerate isomer (14). The structure of diester (8) (indirectl y) and the rearrangement product (14) (directly) are placed on an uneq uivocal base by X-Ray structure analysis. AM1 semi-empirical calculati ons support the preferential formation of (8) from the reaction of DMA D with transient intermediate diene (7). Epoxidation studies (mCPBA) h ave been conducted and firm site selectivities determined. A correctio n is made to an earlier report on the epoxidation selectivity of (18).