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Unexpected Migration of Benzoyl Group in the Synthesis of 3-Benzoyl-2-Phenylbenzofurans under Wittig Conditions

Dipartimento di Scienze della Vita e dell’Ambiente, Università degli Studi di Cagliari, 09124 Cagliari, Italy
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Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November- 15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22.
Proceedings 2019, 9(1), 38; https://doi.org/10.3390/ecsoc-22-05656
Published: 14 November 2018
PDF [237 KB, uploaded 10 April 2019]

Abstract

In the present work, we report the unexpected formation of isomeric 3-benzoyl-2-phenylbenzo[b]furans using triphenylphosphonium salt and benzoyl chlorides under Wittig conditions. In particular, we found that the o-[(benzoyloxy)benzyl]-triphenyl-phosphoranes constitute the key intermediate that reasonably undergoes benzoyl group migration.
Keywords: Wittig reaction; 3-aroyl-2-phenylbenzofurans; phosphorane Wittig reaction; 3-aroyl-2-phenylbenzofurans; phosphorane
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Delogu, G.L.; Begala, M. Unexpected Migration of Benzoyl Group in the Synthesis of 3-Benzoyl-2-Phenylbenzofurans under Wittig Conditions. Proceedings 2019, 9, 38.

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