The reaction of aspirin with base

Sosale Chandrasekhar; Honnaiah Vijay Kumar

doi:10.1016/j.tetlet.2011.04.096

The reaction of aspirin with base

Sosale Chandrasekhar, Honnaiah Vijay Kumar

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	3561-3564
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	28
DOIs	https://doi.org/10.1016/j.tetlet.2011.04.096
State	Published - Jul 13 2011

Bibliographical note

Funding Information:
We thank University Grants Commission (New Delhi) for a D. S. Kothari postdoctoral fellowship to H.V.K. We also remain grateful to a referee for several constructive suggestions which led to a vastly improved manuscript.

Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.

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10.1016/j.tetlet.2011.04.096

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author = "Sosale Chandrasekhar and Kumar, {Honnaiah Vijay}",

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N2 - 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.

AB - 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.

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The reaction of aspirin with base

Abstract

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