Organophosphorous chemistry: Selective transformation of benzoin to benzil, desyl bromide, or benzyl phenyl ketone

Article abstract of DOI:10.1080/10426509808045488

Reaction of benzoin with dibromotriphenylphosphorane under various conditions has been closely investigated. Benzoin was selectively converted to desyl bromide by treatment with dibromotriphenylphosphorane in the presence of triethylamine, while benzyl phenyl ketone was formed in the presence of an excess amount of triphenylphosphine. On the other hand, benzoin was effectively oxidized to benzil by treatment with only bromine. The mechanism of producing these was also proposed. Desyl bromide was formed from the reaction of benzoin with dibromotriphenylphosphorane as a primary product and converted to benzyl phenyl ketone via the Perkow reaction, and benzil was formed by the oxidation of benzoin by bromine. When triethylamine or triphenylphosphine was used as an added base, these bases trapped free bromine, and the oxidation product, benzil, was formed in low yield. In the presence of triphenylphosphine as a base, the Perkow reaction of desyl bromide proceeded smoothly to give benzyl phenyl ketone preferentially, while in the presence of triethylamine, replacement of the hydroxy group to bromide occurred mainly.

Full text of DOI:10.1080/10426509808045488

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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ORGANOPHOSPHOROUS
CHEMISTRY: SELECTIVE
TRANSFORMATION OF BENZOIN
TO BENZIL, DESYL BROMIDE, OR
BENZYL PHENYL KETONE
Isao Furukawa a , Mitsuhiro Sasaki a , Takeshi Inoue a
& Tetsuo Ohta a
a Department of Molecular Science and Technology,
Faculty of Engineering, Doshi-sha University,
Kyotanabe, Kyoto, 610-0394, Japan
Version of record first published: 04 Oct 2006
To cite this article: Isao Furukawa, Mitsuhiro Sasaki, Takeshi Inoue & Tetsuo Ohta
(1998): ORGANOPHOSPHOROUS CHEMISTRY: SELECTIVE TRANSFORMATION OF BENZOIN
TO BENZIL, DESYL BROMIDE, OR BENZYL PHENYL KETONE, Phosphorus, Sulfur, and
Silicon and the Related Elements, 143:1, 85-99
To link to this article: http://dx.doi.org/10.1080/10426509808045488
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