[1,3] and [3,3] rearrangements of 3-amino-1,5-hexadienes: Solvent effect on the regioselectivity

Authors
Dobson, HK LeBlanc, R Perrier, H Stephenson, C Welch, TR Macdonald, D
Citation
Hk. Dobson et al., [1,3] and [3,3] rearrangements of 3-amino-1,5-hexadienes: Solvent effect on the regioselectivity, TETRAHEDR L, 40(16), 1999, pp. 3119-3122
Citations number
5
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
16
Year of publication
1999
Pages
3119 - 3122
Database
ISI
SICI code
0040-4039(19990416)40:16<3119:[A[RO3>2.0.ZU;2-X
Abstract
3-Amino-1,5-Hexadienes rearrange under anionic conditions to give a [1,3] p roduct in addition to the [3,3] (Cope) product. With some substrates the re gioselectivity of the reaction is strongly influenced by the solvent polari ty. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.