Sometimes, the Least Demanding Solution Is the Most Suitable: A Careful Survey of NMR Spectra of a Phosphonium Salt Accounted for Its "Unusual Wittig Reaction"

Anna Fantinati; Paolo Marchetti; Claudio Trapella; Vinicio Zanirato

doi:10.1021/acsomega.8b01228

Sometimes, the Least Demanding Solution Is the Most Suitable: A Careful Survey of NMR Spectra of a Phosphonium Salt Accounted for Its "Unusual Wittig Reaction"

ACS Omega. 2018 Jul 19;3(7):8091-8096. doi: 10.1021/acsomega.8b01228. eCollection 2018 Jul 31.

Authors

Anna Fantinati¹, Paolo Marchetti¹, Claudio Trapella¹, Vinicio Zanirato¹

Affiliation

¹ Department of Chemical and Pharmaceutical Sciences, University of Ferrara, Via Fossato di Mortara 17, I-44121 Ferrara, Italy.

Abstract

Careful product analysis in combination with appropriate supporting experiments unambiguously proves that in contrast to what was previously reported, generation of the phosphonium salt from a β-cyclocitral-derived allylic alcohol and PPh₃HBr takes place via a proton-driven elimination/addition path.