OBSERVATIONS ON THE SYNTHESIS OF FUNCTIONALIZED METHYLENEAZIRIDINES

Authors
INCE J ROSS TM SHIPMAN M SLAWIN AMZ ENNIS DS
Citation
J. Ince et al., OBSERVATIONS ON THE SYNTHESIS OF FUNCTIONALIZED METHYLENEAZIRIDINES, Tetrahedron, 52(20), 1996, pp. 7037-7044
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
20
Year of publication
1996
Pages
7037 - 7044
Database
ISI
SICI code
0040-4020(1996)52:20<7037:OOTSOF>2.0.ZU;2-M
Abstract
N-Triphenylmethyl-2-methyleneaziridine 8 was synthesised from N-(2-bro mo-2-propenyl)-amine 7 by treatment with sodium amide in liquid ammoni a and its structure established using x-ray crystallography. Using mod ified conditions, (S)-N-(1-phenylethyl)-2-methyleneaziridine 9 was pre pared in enantiomerically enriched form. Studies directed towards the synthesis of N-tosyl and N-Boc methyleneaziridines 14 and 15 respectiv ely reveal limitations with this methodology. Copyright (C) 1996 Elsev ier Science Ltd