Abstract
The selective N-monoderivatization of propane-1,3-diamine (5) with carbonyl and sulfonyl chlorides via2-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.
Jentgens, Christian