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Selective monoderivatization of propane-1,3-diamine with acid chlorides: ‘Hexahydropyrimidine method’ vs. statistic methods


Jentgens, Christian; Bienz, Stefan; Hesse, Manfred (1997). Selective monoderivatization of propane-1,3-diamine with acid chlorides: ‘Hexahydropyrimidine method’ vs. statistic methods. Helvetica Chimica Acta, 80(4):1133-1143.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:30 June 1997
Deposited On:24 Aug 2017 16:02
Last Modified:25 Aug 2017 07:38
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.19970800410

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