FUNCTIONALIZED CHLOROENAMINES IN AMINOCYCLOPROPANE SYNTHESIS .13. AZAANNULATED CYCLOPROPANES - RIGID BUILDING-BLOCKS FOR OLIGOAMINES

Authors
SEIBEL J VILSMAIER E FROHLICH K MAAS G WAGEMANN R
Citation
J. Seibel et al., FUNCTIONALIZED CHLOROENAMINES IN AMINOCYCLOPROPANE SYNTHESIS .13. AZAANNULATED CYCLOPROPANES - RIGID BUILDING-BLOCKS FOR OLIGOAMINES, Tetrahedron, 50(3), 1994, pp. 715-730
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
3
Year of publication
1994
Pages
715 - 730
Database
ISI
SICI code
0040-4020(1994)50:3<715:FCIAS.>2.0.ZU;2-M
Abstract
Oligoamines 5, 6 and 7 with rigid 3-azabicyclo[3.1.0]hexyl building bl ocks were synthesized from di(chloroenamines) 8 and nucleophiles. Sodi um borohydride as nucleophile led to endo,endo-tetramines 5a,b; the sa me stereochemical result generating 5d and 5f was observed for cyanide or methyllithium as reagents. Methylmagnesium bromide reacted with 8 to give mainly exo,exo-tetramine 7f besides small amounts of isomers 5 f and 6f. Basicity, conformation and molecular flexibility of the new tetramines 5 - 7 were studied. X-Ray structural analyses pointed out a meander shape of tetramine 5f and a linear arrangement of tetramine 7 f.