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^*

^*此作品的通讯作者

科研成果: 期刊稿件 › 文章 › 同行评审

6 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	948-952
页数	5
期刊	Photochemical and Photobiological Sciences
卷	14
期	5
DOI	https://doi.org/10.1039/c5pp00009b
出版状态	已出版 - 1 5月 2015
已对外发布	是

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title = "A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones",

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 - Sun, Qiu

AU - Yao, Chang Jiang

AU - König, Burkhard

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

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