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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 5
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Original Articles

A Peculiar Reaction of Aminoallenes with Aromatic and Heteroaromatic Aldehydes

R. Nijs Department of Preparative Organic Chemistry of, the University, Debye Institute, Padualaan 8, 3584, CH, Utrecht, The Netherlands
,
H. D. Verkruijsse Department of Preparative Organic Chemistry of, the University, Debye Institute, Padualaan 8, 3584, CH, Utrecht, The Netherlands
,
S. Harder Department of Preparative Organic Chemistry of, the University, Debye Institute, Padualaan 8, 3584, CH, Utrecht, The Netherlands
,
A. C.H. T. M. van der Kerk Department of Preparative Organic Chemistry of, the University, Debye Institute, Padualaan 8, 3584, CH, Utrecht, The Netherlands
&
L. Brandsma Department of Preparative Organic Chemistry of, the University, Debye Institute, Padualaan 8, 3584, CH, Utrecht, The Netherlands
Pages 653-656 | Received 07 Jan 1991, Published online: 23 Sep 2006
 
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Abstract

Addition of the Allenic amine H2C═C═CHNMe2 and the corresponding N-morpholinoallene to a solution of an aromatic or heteroaromatic aldehyde, RCH═O, and lithium bromide in tetrahydrofuran followed by treatment of the reaction mixture with a small amount of acetic acid at elevated temperatures affords the aldehydes RCH═C(CH2NR'2)CH═O (NR'2=NMe2 or morpholino) in reasonable yields.

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