Premium
A New Entry to Bis‐Tröger’s Bases
Author(s) -
Mas Thierry,
Pardo Carmen,
Salort Francisca,
Elguero José,
Torres M. Rosario
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300645
Subject(s) - chemistry , yield (engineering) , nitro , mass spectrometry , base (topology) , nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , organic chemistry , chromatography , mathematical analysis , alkyl , materials science , mathematics , metallurgy
This paper reports the use of p ‐phenylenediamine to prepare bis‐Tröger’s bases. The methyl,nitro‐substituted bis‐Tröger’s base 5 , already previously prepared by another procedure, was obtained in fewer steps, although with no improvement in the yield of the desired syn isomer. The symmetric dinitro‐substituted bis‐Tröger’s base 17 , which cannot be prepared by the older method, was then synthesized. Its structure was determined by mass spectrometry, 2D NMR spectroscopy, and, in the case of the syn isomer, by X‐ray crystallography. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)