CIDNP as a tool to unveil the reaction mechanism: interaction of mixed phosphonium-iodonium ylide with p-methoxyphenylacetylene

Irina I Levina; Valery F Tarasov; Tatyana A Podrugina; Tatiana D Nekipelova

doi:10.1039/c9ra05697a

CIDNP as a tool to unveil the reaction mechanism: interaction of mixed phosphonium-iodonium ylide with p-methoxyphenylacetylene

RSC Adv. 2019 Aug 21;9(45):26219-26223. doi: 10.1039/c9ra05697a. eCollection 2019 Aug 19.

Authors

Irina I Levina¹, Valery F Tarasov², Tatyana A Podrugina^{1

3}, Tatiana D Nekipelova¹

Affiliations

¹ Emanuel Institute of Biochemical Physics RAS Kosygin St. 4 Moscow 119334 Russia nekip@sky.chph.ras.ru.
² Semenov Institute of Chemical Physics RAS Kosygin St. 4 Moscow 119991 Russia.
³ Department of Chemistry, Lomonosov Moscow State University Lenin Hills 1 Moscow 119991 Russia.

Abstract

In situ acquisition of the reaction between benzoyl phosphonium-iodonium ylide and p-methoxyphenylacetylene in an NMR spectrometer reveals the CIDNP effect in ³¹P and ¹H NMR spectra of major products, substituted furan (emission) and phosphonium salt (enhanced absorption). The mechanism of products formation via radical pairs is discussed.