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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
Author(s) -
Jensen Jacob,
Strozyk Michal,
Warnmark Kenneth
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400230
Subject(s) - paraformaldehyde , chemistry , stoichiometry , base (topology) , condensation , scale (ratio) , condensation reaction , organic chemistry , catalysis , thermodynamics , mathematical analysis , physics , mathematics , quantum mechanics
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.