N-methylanilines from benzylic azides

Authors
Lopez, FJ Nitzan, D
Citation
Fj. Lopez et D. Nitzan, N-methylanilines from benzylic azides, TETRAHEDR L, 40(11), 1999, pp. 2071-2074
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
11
Year of publication
1999
Pages
2071 - 2074
Database
ISI
SICI code
0040-4039(19990312)40:11<2071:NFBA>2.0.ZU;2-I
Abstract
Benzylic azides are converted into N-methylanilines efficiently in the pres ence of a Bronsted or Lewis acid and Et3SiH. The combination of SnCl4/Et3Si H and 4-n-butylbenzyl azide appears to form an aminodiazonium trichlorostan nate(II), which undergoes the rearrangement to an iminium salt that is then reduced to N-methyl-4-n-butylaniline by Et3SiH. (C) 1999 Elsevier Science Ltd. All rights reserved.