IN-SITU NMR SPECTROSCOPIC STUDIES OF ANILINE ORTHO ACYLATION (SUGASAWA REACTION) - THE NATURE OF REACTION INTERMEDIATES AND LEWIS-ACID INFLUENCE ON YIELD

Authors
DOUGLAS AW ABRAMSON NL HOUPIS IN KARADY S MOLINA A XAVIER LC YASUDA N
Citation
Aw. Douglas et al., IN-SITU NMR SPECTROSCOPIC STUDIES OF ANILINE ORTHO ACYLATION (SUGASAWA REACTION) - THE NATURE OF REACTION INTERMEDIATES AND LEWIS-ACID INFLUENCE ON YIELD, Tetrahedron letters, 35(37), 1994, pp. 6807-6810
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
37
Year of publication
1994
Pages
6807 - 6810
Database
ISI
SICI code
0040-4039(1994)35:37<6807:INSSOA>2.0.ZU;2-Q
Abstract
Ortho acylation of anilines by nitriles in the presence of BCl3 and a second Lewis acid appear to proceed through an intermediate 'supercomp lex' including ail four components. Yield improvements were obtained b ased on recognition that chloride affinity of the second Lewis acid go verns supercomplex formation. Aniline protonation was found to be the cause of incomplete reaction.