Preparation and Cyclopropanation of selected oxapolycycles

Authors
Sander, M Dehmlow, EV Neumann, B Stammler, HG
Citation
M. Sander et al., Preparation and Cyclopropanation of selected oxapolycycles, TETRAHEDRON, 55(47), 1999, pp. 13395-13406
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
47
Year of publication
1999
Pages
13395 - 13406
Database
ISI
SICI code
0040-4020(19991119)55:47<13395:PACOSO>2.0.ZU;2-U
Abstract
The Diels-Alder reaction of dimethyl furandicarboxylate 6 with DMAD is inve stigated and the exo-exo bisadduct 8 is fully characterized. Monoadduct 7, 8, and test system 12 are cyclopropanated with diazomethane giving 10, 11, and 14. Then 7, 8, and 12 are treated with the "latently acceptor substitut ed" diazomethane 17. After appropriate transformations cyanocyclopropyl der ivatives 18 and 19 are obtained from 7 and 12. Unexpectedly, 8 also gives 1 9 by a retro-Diels-Alder reaction thereby frustrating planned further work. (C) 1999 Elsevier Science Ltd. All rights reserved.