Tetrahedron Letters

Fluorodecarboxylation, rearrangement and cyclisation: the influence of structure and environment on the reactions of carboxylic acids with xenon difluoride

CA Ramsden, MM Shaw

Index: Ramsden, Christopher A.; Shaw, Maxine M. Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3321 - 3324

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Citation Number: 17

Abstract

The reactions of structurally diverse carboxylic acids with XeF2 in both CH2Cl2/Pyrex® and CH2Cl2/PTFE have been studied. Pyrex® appears to be a very effective heterogeneous catalyst for an electrophilic mode of reaction of polarised XeF2, leading to rearrangement, cyclisation and cationic products. In CH2Cl2/PTFE, fluorodecarboxylation is the main mode of reaction, in accordance with previous studies, and may occur via a SET reaction of ...

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