Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: A non-singlet-oxygen mechanism

Tadashi Mori; Makoto Takamoto; Yoshimasa Tate; Junya Shinkuma; Takehiko Wada; Yoshihisa Inoue

doi:10.1016/S0040-4039(01)00213-1

Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: A non-singlet-oxygen mechanism

Tadashi Mori, Makoto Takamoto, Yoshimasa Tate, Junya Shinkuma, Takehiko Wada, Yoshihisa Inoue

IMRAM - Division of Organic- and Biomaterials Research

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

21 Citations (Scopus)

Abstract

α-Methylstyrene (1) was photooxidized with oxygen in the presence of a series of alkylated dimethoxybenzenes as a sensitizer in acetonitrile, affording the cleaved ketone (2), epoxide (3) as well as a small amount of the ene product (4) in ca. 1:1:0.04 ratio. A non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by oxygen to produce a sensitizer radical cation and a superoxide ion (O₂^·-), the former of which oxidizes 1, while O₂^·- reacts with the resulting 1^·+ to give the major oxidation products.

Original language	English
Pages (from-to)	2505-2508
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4039(01)00213-1
Publication status	Published - 2001 Mar 26

Keywords

α-methylstyrene
Dimethoxybenzenes
Electron transfer oxidation
Molecular oxygen
Non-singlet-oxygen mechanism

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10.1016/S0040-4039(01)00213-1

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@article{708ee6d6864548209fb93f5a4b01ed39,

title = "Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: A non-singlet-oxygen mechanism",

abstract = "α-Methylstyrene (1) was photooxidized with oxygen in the presence of a series of alkylated dimethoxybenzenes as a sensitizer in acetonitrile, affording the cleaved ketone (2), epoxide (3) as well as a small amount of the ene product (4) in ca. 1:1:0.04 ratio. A non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by oxygen to produce a sensitizer radical cation and a superoxide ion (O2·-), the former of which oxidizes 1, while O2·- reacts with the resulting 1·+ to give the major oxidation products.",

keywords = "α-methylstyrene, Dimethoxybenzenes, Electron transfer oxidation, Molecular oxygen, Non-singlet-oxygen mechanism",

author = "Tadashi Mori and Makoto Takamoto and Yoshimasa Tate and Junya Shinkuma and Takehiko Wada and Yoshihisa Inoue",

note = "Funding Information: Financial support (to T.M.) of this work by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture of Japan (No. 12740346) and from the Shorai Foundation for Science and Technology are gratefully acknowledged.",

year = "2001",

month = mar,

day = "26",

doi = "10.1016/S0040-4039(01)00213-1",

language = "English",

volume = "42",

pages = "2505--2508",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "13",

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TY - JOUR

T1 - Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes

T2 - A non-singlet-oxygen mechanism

AU - Mori, Tadashi

AU - Takamoto, Makoto

AU - Tate, Yoshimasa

AU - Shinkuma, Junya

AU - Wada, Takehiko

AU - Inoue, Yoshihisa

N1 - Funding Information: Financial support (to T.M.) of this work by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture of Japan (No. 12740346) and from the Shorai Foundation for Science and Technology are gratefully acknowledged.

PY - 2001/3/26

Y1 - 2001/3/26

N2 - α-Methylstyrene (1) was photooxidized with oxygen in the presence of a series of alkylated dimethoxybenzenes as a sensitizer in acetonitrile, affording the cleaved ketone (2), epoxide (3) as well as a small amount of the ene product (4) in ca. 1:1:0.04 ratio. A non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by oxygen to produce a sensitizer radical cation and a superoxide ion (O2·-), the former of which oxidizes 1, while O2·- reacts with the resulting 1·+ to give the major oxidation products.

AB - α-Methylstyrene (1) was photooxidized with oxygen in the presence of a series of alkylated dimethoxybenzenes as a sensitizer in acetonitrile, affording the cleaved ketone (2), epoxide (3) as well as a small amount of the ene product (4) in ca. 1:1:0.04 ratio. A non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by oxygen to produce a sensitizer radical cation and a superoxide ion (O2·-), the former of which oxidizes 1, while O2·- reacts with the resulting 1·+ to give the major oxidation products.

KW - α-methylstyrene

KW - Dimethoxybenzenes

KW - Electron transfer oxidation

KW - Molecular oxygen

KW - Non-singlet-oxygen mechanism

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U2 - 10.1016/S0040-4039(01)00213-1

DO - 10.1016/S0040-4039(01)00213-1

M3 - Article

AN - SCOPUS:0035952977

SN - 0040-4039

VL - 42

SP - 2505

EP - 2508

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: A non-singlet-oxygen mechanism

Abstract

Keywords

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