Photoinduced reactions of 3β-acetoxycholesta-5,7-diene, 3β-acetoxycholest-5-ene, tetraphenylcyclopentadiene and 1,1-diphenylethylene with oxygen in the presence of phenylselenenyl bromide

Richard K. Haynes; Audrey E. Hilliker

doi:10.1016/S0040-4039(00)85518-5

Photoinduced reactions of 3β-acetoxycholesta-5,7-diene, 3β-acetoxycholest-5-ene, tetraphenylcyclopentadiene and 1,1-diphenylethylene with oxygen in the presence of phenylselenenyl bromide

Richard K. Haynes^*, Audrey E. Hilliker

^*Corresponding author for this work

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

8 Citations (Scopus)

Abstract

Whereas PhSeBr under irradiation with O₂ in CH₂Cl₂ at -78° acts as a photoxygenation catalyst to convert 3 β-acetoxycholesta-5,7-diene and tetraphenylcyclopentadiene into the corresponding endoperoxides, and 3β-acetoxycholest-5-ene into 3β-acetoxycholest-5-en-7-one and the corresponding alcohols, it reacts with 1,1-diphenylethylene to give mainly a bromohydrin; bromine radicals arising by photodissociation of the PhSeBr are implicated as the active intermediates.

Original language	English
Pages (from-to)	509-512
Number of pages	4
Journal	Tetrahedron Letters
Volume	27
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4039(00)85518-5
Publication status	Published - 1986
Externally published	Yes

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@article{baed8cc68da740bca4501c99fcd57a5f,

title = "Photoinduced reactions of 3β-acetoxycholesta-5,7-diene, 3β-acetoxycholest-5-ene, tetraphenylcyclopentadiene and 1,1-diphenylethylene with oxygen in the presence of phenylselenenyl bromide",

abstract = "Whereas PhSeBr under irradiation with O2 in CH2Cl2 at -78° acts as a photoxygenation catalyst to convert 3 β-acetoxycholesta-5,7-diene and tetraphenylcyclopentadiene into the corresponding endoperoxides, and 3β-acetoxycholest-5-ene into 3β-acetoxycholest-5-en-7-one and the corresponding alcohols, it reacts with 1,1-diphenylethylene to give mainly a bromohydrin; bromine radicals arising by photodissociation of the PhSeBr are implicated as the active intermediates.",

author = "Haynes, \{Richard K.\} and Hilliker, \{Audrey E.\}",

year = "1986",

doi = "10.1016/S0040-4039(00)85518-5",

language = "English",

volume = "27",

pages = "509--512",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "4",

}

TY - JOUR

T1 - Photoinduced reactions of 3β-acetoxycholesta-5,7-diene, 3β-acetoxycholest-5-ene, tetraphenylcyclopentadiene and 1,1-diphenylethylene with oxygen in the presence of phenylselenenyl bromide

AU - Haynes, Richard K.

AU - Hilliker, Audrey E.

PY - 1986

Y1 - 1986

N2 - Whereas PhSeBr under irradiation with O2 in CH2Cl2 at -78° acts as a photoxygenation catalyst to convert 3 β-acetoxycholesta-5,7-diene and tetraphenylcyclopentadiene into the corresponding endoperoxides, and 3β-acetoxycholest-5-ene into 3β-acetoxycholest-5-en-7-one and the corresponding alcohols, it reacts with 1,1-diphenylethylene to give mainly a bromohydrin; bromine radicals arising by photodissociation of the PhSeBr are implicated as the active intermediates.

AB - Whereas PhSeBr under irradiation with O2 in CH2Cl2 at -78° acts as a photoxygenation catalyst to convert 3 β-acetoxycholesta-5,7-diene and tetraphenylcyclopentadiene into the corresponding endoperoxides, and 3β-acetoxycholest-5-ene into 3β-acetoxycholest-5-en-7-one and the corresponding alcohols, it reacts with 1,1-diphenylethylene to give mainly a bromohydrin; bromine radicals arising by photodissociation of the PhSeBr are implicated as the active intermediates.

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:A1986AYF2800027

UR - https://www.scopus.com/pages/publications/0642264153

U2 - 10.1016/S0040-4039(00)85518-5

DO - 10.1016/S0040-4039(00)85518-5

M3 - Journal Article

SN - 0040-4039

VL - 27

SP - 509

EP - 512

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

Photoinduced reactions of 3β-acetoxycholesta-5,7-diene, 3β-acetoxycholest-5-ene, tetraphenylcyclopentadiene and 1,1-diphenylethylene with oxygen in the presence of phenylselenenyl bromide

Abstract

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