Reduction of benzophenone by SmI2: The role of proton donors in determining product distribution

Gregory Kleiner; Alexander Tarnopolsky; Shmaryahu Hoz

doi:10.1021/ol051623q

Reduction of benzophenone by SmI₂: The role of proton donors in determining product distribution

Gregory Kleiner, Alexander Tarnopolsky, Shmaryahu Hoz

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

(Graph Presented) Reduction of benzophenone by SmI₂ yields benzopinacol. Addition of proton donors results in an initial increase in the amount of the benzhydrol formed. However, the ratio benzhydrol/benzopinacol reaches a maximum, decreases, and then levels off as the proton donor concentration is further increased. The position of the maximum and its height depend on the proton donor concentration and its kinetic acidity. The momentary concentration of the intermediate radicals governs the product distribution.

Original language	English
Pages (from-to)	4197-4200
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	19
DOIs	https://doi.org/10.1021/ol051623q
State	Published - 15 Sep 2005

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abstract = "(Graph Presented) Reduction of benzophenone by SmI2 yields benzopinacol. Addition of proton donors results in an initial increase in the amount of the benzhydrol formed. However, the ratio benzhydrol/benzopinacol reaches a maximum, decreases, and then levels off as the proton donor concentration is further increased. The position of the maximum and its height depend on the proton donor concentration and its kinetic acidity. The momentary concentration of the intermediate radicals governs the product distribution.",

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N2 - (Graph Presented) Reduction of benzophenone by SmI2 yields benzopinacol. Addition of proton donors results in an initial increase in the amount of the benzhydrol formed. However, the ratio benzhydrol/benzopinacol reaches a maximum, decreases, and then levels off as the proton donor concentration is further increased. The position of the maximum and its height depend on the proton donor concentration and its kinetic acidity. The momentary concentration of the intermediate radicals governs the product distribution.

AB - (Graph Presented) Reduction of benzophenone by SmI2 yields benzopinacol. Addition of proton donors results in an initial increase in the amount of the benzhydrol formed. However, the ratio benzhydrol/benzopinacol reaches a maximum, decreases, and then levels off as the proton donor concentration is further increased. The position of the maximum and its height depend on the proton donor concentration and its kinetic acidity. The momentary concentration of the intermediate radicals governs the product distribution.

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Reduction of benzophenone by SmI₂: The role of proton donors in determining product distribution

Abstract

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