REARRANGEMENT AND VALENCE ISOMERIZATION IN THE DIMETHYLDIOXIRANE EPOXIDATION OF 2,3,5,6-TETRAMETHOXYBENZOBARRELENE TO BENZONORCARADIENE ENDO-ESTER

Authors
ADAM W AHRWEILER M BALCI M CAKMAK O SAHAMOLLER CR
Citation
W. Adam et al., REARRANGEMENT AND VALENCE ISOMERIZATION IN THE DIMETHYLDIOXIRANE EPOXIDATION OF 2,3,5,6-TETRAMETHOXYBENZOBARRELENE TO BENZONORCARADIENE ENDO-ESTER, Tetrahedron letters, 36(9), 1995, pp. 1429-1430
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
9
Year of publication
1995
Pages
1429 - 1430
Database
ISI
SICI code
0040-4039(1995)36:9<1429:RAVIIT>2.0.ZU;2-Q
Abstract
Oxidation of 2,3,5,6-tetramethoxybenzobarrelene 1 by dimethyldioxirane afforded stereoselectively the endo-2 ester by Wagner-Meerwein rearra ngement, The initially formed benzonorcaradiene endo-2 isomer rearrang ed smoothly at room temperature to the exo-2 isomer by noxcaradiene-tr opylidene valence isomerization. The diastereomeric endo, exo-2 esters gave on dimethyldioxirane oxidation the corresponding anti epoxy este rs 3 in high yield.