Cycloaddition reactions of sodium dinitroxytrioxide (Angeli's salt)

Authors
Torun, L Mohammad, T Morrison, H
Citation
L. Torun et al., Cycloaddition reactions of sodium dinitroxytrioxide (Angeli's salt), TETRAHEDR L, 40(29), 1999, pp. 5279-5282
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
29
Year of publication
1999
Pages
5279 - 5282
Database
ISI
SICI code
0040-4039(19990716)40:29<5279:CROSD(>2.0.ZU;2-X
Abstract
Angeli's salt undergoes a quantitative reaction with 1,3-diphenylisobenzofu ran in a methanol/water solution at room temperature to give a product (1) explicable by an initial [4+2] cycloaddition reaction. Under the same condi tions, Angeli's salt reacts with 1-naphthaldehyde to give 1-naphthoic acid in good yield. This reaction can also be explained by an initial [2+2] cycl oaddition to give a hydroxamic acid, which is then hydrolyzed to the carbox ylic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.