1,3-DIPHENYLPROPAN-1,3-DIAMINES .9. REACTION OF ALPHA-CHLOROOXIME ETHERS WITH ALPHA-LITHIOBENZYLAMINES

Authors
KAISER A WIEGREBE W
Citation
A. Kaiser et W. Wiegrebe, 1,3-DIPHENYLPROPAN-1,3-DIAMINES .9. REACTION OF ALPHA-CHLOROOXIME ETHERS WITH ALPHA-LITHIOBENZYLAMINES, Monatshefte fuer Chemie, 127(6-7), 1996, pp. 763-774
Citations number
27
Categorie Soggetti
Chemistry
Journal title
Monatshefte fuer Chemie → ACNP
ISSN journal
00269247
Volume
127
Issue
6-7
Year of publication
1996
Pages
763 - 774
Database
ISI
SICI code
0026-9247(1996)127:6-7<763:1.ROAE>2.0.ZU;2-S
Abstract
The carbanions of the benzylamine derivatives 1-4 have been reacted wi th alpha-chlorooxime ether 5 in order to gel precursors of 1,3-dipheny lpropane-1,3-diamines. Isonitrile 1 afforded the expected result, wher eas lithiated benzamide 2 underwent oxidative dimerization and transme tallated chlorooxime derivative 5. Isoxazolidine 3 gave the condensati on product 21 as a mixture of diastereomers; treatment of imine 4 led to the desired amine-oxime 15 in low yield.