Nitrile Reversible ketenimine tautomerism in substituted alkylidene malononitriles and alkylidene cyanoacetates: A characteristic UV absorption band

Kasturi, TR and Sharma, VK and Srinivasan, A and Subrahmanyam, G (1973) Nitrile Reversible ketenimine tautomerism in substituted alkylidene malononitriles and alkylidene cyanoacetates: A characteristic UV absorption band. In: Tetrahedron, 29 (24). pp. 4103-4109.

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Abstract

Several alkylidene malononitriles (1b,1d,1e,2b and4b) and alkylidene cyanoacetates (1a,2a and4a) studied exhibit a long wavelength UV absorption band around 355 nm which shows a hyperchromic effect in the presence of ethanolic alkali. This band has been assigned to the ketenimine tautomer (5). Addition of water to1b,1e and2b gives the corresponding pyridine diols (7a,7b and8a) respectively. Similarly, addition of ethanol to1e and2b gave the corresponding ethoxypyridine derivatives (7c and8b). Mechanism of formation of these compounds is discussed. Structures, as well as mechanism of formation of1c,7c and10 obtained from1b,1e and2b respectively on standing at room temperature are also discussed.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier Science
Additional Information:	Copyright of this article belongs to Elsevier Science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	19 Dec 2009 07:25
Last Modified:	19 Sep 2010 05:46
URI:	http://eprints.iisc.ac.in/id/eprint/23580

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