HETEROAROMATIC N-OXIDE REARRANGEMENTS - REINVESTIGATION OF 1,3 TOSYLOXY MIGRATION IN THE REACTION OF ISOQUINOLINE N-OXIDE WITH TOSYL CHLORIDE

Authors
MARYANOFF BE ZHANG HC REITZ AB LEO GC JONES WJ
Citation
Be. Maryanoff et al., HETEROAROMATIC N-OXIDE REARRANGEMENTS - REINVESTIGATION OF 1,3 TOSYLOXY MIGRATION IN THE REACTION OF ISOQUINOLINE N-OXIDE WITH TOSYL CHLORIDE, Tetrahedron letters, 34(45), 1993, pp. 7247-7250
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
45
Year of publication
1993
Pages
7247 - 7250
Database
ISI
SICI code
0040-4039(1993)34:45<7247:HNR-RO>2.0.ZU;2-X
Abstract
Isoquinoline N-oxide (2) reacts with O-18-enriched tosyl chloride to f urnish O-18-labeled 4-tosyloxy-isoquinoline (4), which was assessed fo r oxygen isotopic enrichment by NMR and mass spectrometry. The 30-45% O-18 incorporation at the bridging oxygen is inconsistent with a high level of the intramolecular tight-ion-pair (''sliding'') mechanism. A combination of two intramolecular mechanisms is probably operative.