Tetrahedron letters

Highly selective zeolite-catalysed mono-N-alkylation of arylenediamines by dialkyl carbonates

WJ Ebenezer, MG Hutchings, K Jones, DA Lambert…

Index: Ebenezer, Warren J.; Hutchings, Michael G.; Jones, Ken; Lambert, David A.; Watt, Ian Tetrahedron Letters, 2007 , vol. 48, # 9 p. 1641 - 1643

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Citation Number: 15

Abstract

We now describe an additional useful and more surprising dimension to the selectivity displayed by this reagent combination in the alkylation of arylenediamines. When we initially exposed a phenylenediamine to the NaY-catalysed dialkyl carbonate alkylation reaction conditions, we had expected to observe N,N′-dialkylation. In fact these conditions lead to highly selective—sometimes specific—mono-N-alkylation of just one of the amino groups ...