Application of triazenes for protection of secondary amines

Authors
Lazny, R Sienkiewicz, M Brase, S
Citation
R. Lazny et al., Application of triazenes for protection of secondary amines, TETRAHEDRON, 57(27), 2001, pp. 5825-5832
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
27
Year of publication
2001
Pages
5825 - 5832
Database
ISI
SICI code
0040-4020(20010702)57:27<5825:AOTFPO>2.0.ZU;2-A
Abstract
Use of the phenyldiazenyl group, which serves as a protecting group for sec ondary amines is described in detail. The triazene protected amine is compa tible with oxidative and reductive conditions as well as with strong bases (LDA, tert-butyllithium) and alkylating reagents. The amine is regenerated by action of trifluoroacetic acid and a suitable reducing agent (EtOH or Na H2PO2). (C) 2001 Elsevier Science Ltd. All rights reserved.