Reduction of benzophenones with SmI2. Post electron transfer processes

Hani Farran, Shmaryahu Hoz

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

The kinetics of the reaction of several substituted benzophenones with SmI2 in THF was studied by using stopped flow spectrometry. The electron transfer takes place during the dead time of mixing and for most derivatives it is nearly quantitative. In the presence of an excess of substrate and in the absence of proton donors the dimerization reaction to pinacol is second order in the radical anion and has a negative order in SmI2. Similarly, in reactions in the presence of excess SmI2, the reaction shows negative order in the concentration of the substrate. It is concluded that the radical anions exist as a mixture of monomeric ion pairs and Streitwieser dimers. In the presence of trifluoroethanol, protonation of the Streitwieser dimer occurs with a rate constant an order of magnitude larger than that of the monomer.

Original languageEnglish
Pages (from-to)2075-2079
Number of pages5
JournalJournal of Organic Chemistry
Volume74
Issue number5
DOIs
StatePublished - 6 Mar 2009

Fingerprint

Dive into the research topics of 'Reduction of benzophenones with SmI2. Post electron transfer processes'. Together they form a unique fingerprint.

Cite this