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Influence of scale, stoichiometry and temperature on the synthesis of 2,8-dihalo analogues of tröger's base from the corresponding anilines and paraformaldehyde

✍ Scribed by Jacob Jensen; Michal Strozyk; Kenneth Warnmark

Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 41 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400230

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✦ Synopsis

Abstract

The yields of 2,8‐dihalo analogues of Tröger's base in the condensation between 4‐haloanilines and paraformaldehyde was found to be highly sensitive to the crucial reaction parameters of scale, stoichiometry and temperature. The reaction conditions were optimized allowing for the semi‐large scale synthesis of the 2,8‐diiodo‐ (2) and 2,8‐dibromo‐ (3) analogues, respectively.

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