THEORETICAL AND EXPERIMENTAL STUDIES OF THE 3-AZA-CLAISEN REARRANGEMENT

Authors
GILBERT JC COUSINS KR
Citation
Jc. Gilbert et Kr. Cousins, THEORETICAL AND EXPERIMENTAL STUDIES OF THE 3-AZA-CLAISEN REARRANGEMENT, Tetrahedron, 50(36), 1994, pp. 10671-10684
Citations number
72
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
36
Year of publication
1994
Pages
10671 - 10684
Database
ISI
SICI code
0040-4020(1994)50:36<10671:TAESOT>2.0.ZU;2-K
Abstract
Semiempirical calculations support a spin-paired chair-like TS for the 3-aza-Claisen rearrangement, and yield the prediction that an anionic substituent on the nitrogen atom reduces the activation energies for the rearrangement. Attempts to demonstrate this experimentally have be en unsuccessful.