REACTIONS OF 2,6-DIARYL-3,7-DIOXABICYCLO[3.3.0]OCTANE LIGNANS

Authors
PELTER A WARD RS
Citation
A. Pelter et Rs. Ward, REACTIONS OF 2,6-DIARYL-3,7-DIOXABICYCLO[3.3.0]OCTANE LIGNANS, Heterocycles, 37(1), 1994, pp. 137-147
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
37
Issue
1
Year of publication
1994
Pages
137 - 147
Database
ISI
SICI code
0385-5414(1994)37:1<137:RO2L>2.0.ZU;2-J
Abstract
Reactions of 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans (furofur ans) have been rationalised in terms of the production of stabilised c arbocations. These may be produced by acid catalysed or oxidative reac tions dependant on the constitution of the lignan substrate. The carbo cations may then undergo rearrangements in the case of acid catalysed reactions or the rearrangement products may themselves be further oxid ised. In the presence of triethylsilane the carbocations are reduced p rior to rearrangement.