O-17-LABELING STUDIES ON THE REACTION OF 4-BENZOYL-5-PHENYLFURAN-2,3-DIONE WITH CARBODIIMIDES

Authors
HEILMAYER W STERK H KOLLENZ G
Citation
W. Heilmayer et al., O-17-LABELING STUDIES ON THE REACTION OF 4-BENZOYL-5-PHENYLFURAN-2,3-DIONE WITH CARBODIIMIDES, Tetrahedron, 54(28), 1998, pp. 8025-8034
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
28
Year of publication
1998
Pages
8025 - 8034
Database
ISI
SICI code
0040-4020(1998)54:28<8025:OSOTRO>2.0.ZU;2-Q
Abstract
The reactions of 4-benzoyl-5-phenyl-furan-2,3-dione 1 with isopropyl-p henylcarbodiimide as well as dimethylcarbodiimide are investigated wit h aid of O-17-labeling experiments. From comparing the distribution of the label within starting materials and products, an unusual furandio ne rearrangement is disclosed. This rearrangement can be regarded as a peculiar variation of the well known nucleophilic substitution at a v inylic carbon. (C) 1998 Elsevier Science Ltd. All rights reserved.