Synthesis 2005(4): 543-546  
DOI: 10.1055/s-2004-837290
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient and Selective One-Pot Method for the Synthesis of Monosubstituted Secondary Alkyl Malononitriles

Robert E. Sammelson*, Mark J. Allen
Department of Chemistry, Ball State University, Muncie, Indiana, 47306-0445, USA
Fax: +1(765)2856505; e-Mail: resammelson@bsu.edu;
Further Information

Publication History

Received 12 July 2004
Publication Date:
16 December 2004 (eFirst)

Abstract

We have found that α,α-dicyanoalkenes can be efficiently and selectively reduced to α,α-dicyanoalkanes (malononitriles) with NaBH4 in 95% EtOH at 0 °C. In addition, we have determined that the condensation of malononitrile with ketones using absorption alumina as a catalyst can be followed directly, in one pot, by reduction with NaBH4 in 95% EtOH at 0 °C to provide the monosubstituted secondary alkyl malononitriles in good to excellent yields (42-94%). This procedure provides a convenient alternative to direct alkylation of malononitrile or reduction of α,α-dicyanoalkene intermediates.

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