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The reaction of aspirin with base

Chandrasekhar, Sosale and Kumar, Honnaiah Vijay (2011) The reaction of aspirin with base. In: Tetrahedron Letters, 52 (28). pp. 3561-3564.

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2011.04.096


Aspirin anion appears to exist only fleetingly, rearranging via acetyl transfer to the ortho carboxylate group, as indicated by IR, UV and NMR. The resulting mixed anhydride cyclises to the more stable bicyclic orthoacetate isomer, a process facilitated by time and increasing pH. Mechanistic possibilities are discussed to explain these intriguing observations. (C) 2011 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Publication: Tetrahedron Letters
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 18 Jul 2011 09:35
Last Modified: 18 Jul 2011 09:35
URI: http://eprints.iisc.ac.in/id/eprint/39187

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