Rearrangement during halogenation of 2-hydroxy-1,2-diphenylpropan-1-one (α-methylbenzoin)

Kati Marianne Aitken; Robert Alan Aitken

doi:10.1016/j.tet.2008.03.043

Rearrangement during halogenation of 2-hydroxy-1,2-diphenylpropan-1-one (α-methylbenzoin)

Kati Marianne Aitken, Robert Alan Aitken

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

Abstract

The reaction of 2-hydroxy-1,2-diphenylpropan-1-one 1 with SOCl2 or PBr3 gives, respectively, the 3-chloro- and 3-bromo-1,2-diphenylpropan-1-ones 4 and 6. The expected 2-chloro- and 2-bromo-1,2-diphenylpropan-1-ones 2 and 5 can, however, be formed by treatment of 1,2-diphenylpropan-1-one 8 with Cl-2 or Br-2/AlCl3. The four halogenated products are characterised by H-1 and C-13 NMR spectroscopy for the first time. (c) 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5217-5220
Number of pages	4
Journal	Tetrahedron
Volume	64
DOIs	https://doi.org/10.1016/j.tet.2008.03.043
Publication status	Published - 26 May 2008

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KETONES

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10.1016/j.tet.2008.03.043

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title = "Rearrangement during halogenation of 2-hydroxy-1,2-diphenylpropan-1-one (α-methylbenzoin)",

abstract = "The reaction of 2-hydroxy-1,2-diphenylpropan-1-one 1 with SOCl2 or PBr3 gives, respectively, the 3-chloro- and 3-bromo-1,2-diphenylpropan-1-ones 4 and 6. The expected 2-chloro- and 2-bromo-1,2-diphenylpropan-1-ones 2 and 5 can, however, be formed by treatment of 1,2-diphenylpropan-1-one 8 with Cl-2 or Br-2/AlCl3. The four halogenated products are characterised by H-1 and C-13 NMR spectroscopy for the first time. (c) 2008 Elsevier Ltd. All rights reserved.",

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author = "Aitken, \{Kati Marianne\} and Aitken, \{Robert Alan\}",

year = "2008",

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language = "English",

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T1 - Rearrangement during halogenation of 2-hydroxy-1,2-diphenylpropan-1-one (α-methylbenzoin)

AU - Aitken, Kati Marianne

AU - Aitken, Robert Alan

PY - 2008/5/26

Y1 - 2008/5/26

N2 - The reaction of 2-hydroxy-1,2-diphenylpropan-1-one 1 with SOCl2 or PBr3 gives, respectively, the 3-chloro- and 3-bromo-1,2-diphenylpropan-1-ones 4 and 6. The expected 2-chloro- and 2-bromo-1,2-diphenylpropan-1-ones 2 and 5 can, however, be formed by treatment of 1,2-diphenylpropan-1-one 8 with Cl-2 or Br-2/AlCl3. The four halogenated products are characterised by H-1 and C-13 NMR spectroscopy for the first time. (c) 2008 Elsevier Ltd. All rights reserved.

AB - The reaction of 2-hydroxy-1,2-diphenylpropan-1-one 1 with SOCl2 or PBr3 gives, respectively, the 3-chloro- and 3-bromo-1,2-diphenylpropan-1-ones 4 and 6. The expected 2-chloro- and 2-bromo-1,2-diphenylpropan-1-ones 2 and 5 can, however, be formed by treatment of 1,2-diphenylpropan-1-one 8 with Cl-2 or Br-2/AlCl3. The four halogenated products are characterised by H-1 and C-13 NMR spectroscopy for the first time. (c) 2008 Elsevier Ltd. All rights reserved.

KW - KETONES

UR - https://www.scopus.com/pages/publications/42749092163

U2 - 10.1016/j.tet.2008.03.043

DO - 10.1016/j.tet.2008.03.043

M3 - Article

SN - 0040-4020

VL - 64

SP - 5217

EP - 5220

JO - Tetrahedron

JF - Tetrahedron

ER -

Rearrangement during halogenation of 2-hydroxy-1,2-diphenylpropan-1-one (α-methylbenzoin)

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