A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones

Qiu Sun; Chang Jiang Yao; Burkhard König

doi:10.1039/c5pp00009b

A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones

Qiu Sun, Chang Jiang Yao, Burkhard König^*

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

Aryl chalcones rearrange and add methanol to give substituted propane-1-ones upon UV-A irradiation in the presence of PPh₃. We propose two possible mechanisms for this photo-rearrangement. The reaction involves either the formation of a phosphine-carbonyl intermediate, nucleophilic addition of MeOH and 1,2-aryl migration or the formation of ylide and carbene intermediates. The intermediates trapped from the reaction mixture support the first mechanistic hypothesis.

Original language	English
Pages (from-to)	948-952
Number of pages	5
Journal	Photochemical and Photobiological Sciences
Volume	14
Issue number	5
DOIs	https://doi.org/10.1039/c5pp00009b
Publication status	Published - 1 May 2015
Externally published	Yes

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abstract = "Aryl chalcones rearrange and add methanol to give substituted propane-1-ones upon UV-A irradiation in the presence of PPh3. We propose two possible mechanisms for this photo-rearrangement. The reaction involves either the formation of a phosphine-carbonyl intermediate, nucleophilic addition of MeOH and 1,2-aryl migration or the formation of ylide and carbene intermediates. The intermediates trapped from the reaction mixture support the first mechanistic hypothesis.",

author = "Qiu Sun and Yao, {Chang Jiang} and Burkhard K{\"o}nig",

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AU - Yao, Chang Jiang

AU - König, Burkhard

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PY - 2015/5/1

Y1 - 2015/5/1

N2 - Aryl chalcones rearrange and add methanol to give substituted propane-1-ones upon UV-A irradiation in the presence of PPh3. We propose two possible mechanisms for this photo-rearrangement. The reaction involves either the formation of a phosphine-carbonyl intermediate, nucleophilic addition of MeOH and 1,2-aryl migration or the formation of ylide and carbene intermediates. The intermediates trapped from the reaction mixture support the first mechanistic hypothesis.

AB - Aryl chalcones rearrange and add methanol to give substituted propane-1-ones upon UV-A irradiation in the presence of PPh3. We propose two possible mechanisms for this photo-rearrangement. The reaction involves either the formation of a phosphine-carbonyl intermediate, nucleophilic addition of MeOH and 1,2-aryl migration or the formation of ylide and carbene intermediates. The intermediates trapped from the reaction mixture support the first mechanistic hypothesis.

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U2 - 10.1039/c5pp00009b

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A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones

Abstract

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