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Selective Monoderivatization of Propane‐1,3‐diamine with Acid Chlorides: ‘Hexahydropyrimidine method’ vs. statistic methods
Author(s) -
Jentgens Christian,
Bienz Stefan,
Hesse Manfred
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800410
Subject(s) - chemistry , propane , statistic , sulfonyl , diamine , reactivity (psychology) , medicinal chemistry , organic chemistry , statistics , mathematics , medicine , alkyl , alternative medicine , pathology
The selective N ‐monoderivatization of propane‐1,3‐diamine ( 5 ) with carbonyl and sulfonyl chlorides via 2‐phenylhexahydropyrimidine ( 6 ) was compared with the direct statistic monoderivatization. It was found that, under optimized conditions, both methods are competitive to one another, depending, however, strongly on the reactivity of the eleclrophile used. The ‘hexahydropyrimidine method’ is more reliable with respect to yields, which are moderate but invariably between 54 and 69%, whereas the ‘statistic method’ leads in certain cases to exceptionally high yields (up to 96%), in others, however, almost none.