Formation of sulfur-centered cation radicals by photofragmentation

Richard S. Glass; Jeffrey L. Broeker; Elke Anklam; Klaus Dieter Asmus

doi:10.1016/S0040-4039(00)91715-5

Formation of sulfur-centered cation radicals by photofragmentation

Richard S. Glass
, Jeffrey L. Broeker
, Elke Anklam
, Klaus Dieter Asmus

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

6 Scopus citations

Abstract

The selected dialkyl dithioethers 1,5-dithiocane, 1,4-dithiepane, 1,4-dithiane, and 2,6-dithiaheptane are readily monoalkylated in nitromethane by tert-butyl O-trifluoromethanesulfonyl-3-hydroxyperoxypropanoate, 6, to give the corresponding sulfonium salt peresters 2a-c, and 3 in good yield. Laser flash photolysis of these compounds affords the known two-sulfur, three-electron stabilized cation radicals 2a, b, and 5 which were characterized by optical absorption spectroscopy.

Original language	English (US)
Pages (from-to)	1721-1724
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4039(00)91715-5
State	Published - Mar 24 1992
Externally published	Yes

Keywords

Sulfur-centered cation radical formation
laser flash photolysis
perester fragmentation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)91715-5

Cite this

@article{6f95a1c01c4946d988f9ada4b0a5423f,

title = "Formation of sulfur-centered cation radicals by photofragmentation",

abstract = "The selected dialkyl dithioethers 1,5-dithiocane, 1,4-dithiepane, 1,4-dithiane, and 2,6-dithiaheptane are readily monoalkylated in nitromethane by tert-butyl O-trifluoromethanesulfonyl-3-hydroxyperoxypropanoate, 6, to give the corresponding sulfonium salt peresters 2a-c, and 3 in good yield. Laser flash photolysis of these compounds affords the known two-sulfur, three-electron stabilized cation radicals 2a, b, and 5 which were characterized by optical absorption spectroscopy.",

keywords = "Sulfur-centered cation radical formation, laser flash photolysis, perester fragmentation",

author = "Glass, \{Richard S.\} and Broeker, \{Jeffrey L.\} and Elke Anklam and Asmus, \{Klaus Dieter\}",

note = "Funding Information: Acknowledgment: RSG and JLB gratefullya cknowledges upport of this work by the U.S. Public Health Service,N ational Institutes of Health, Grant No. HL 15104. Part of this work was conducted with the help of Dr. S. Steenken at the Max Planck Institut fir Strahlenchemie( Maheim), which E.A. thanks for its gracioush ospitality.",

year = "1992",

month = mar,

day = "24",

doi = "10.1016/S0040-4039(00)91715-5",

language = "English (US)",

volume = "33",

pages = "1721--1724",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "13",

}

TY - JOUR

T1 - Formation of sulfur-centered cation radicals by photofragmentation

AU - Glass, Richard S.

AU - Broeker, Jeffrey L.

AU - Anklam, Elke

AU - Asmus, Klaus Dieter

N1 - Funding Information: Acknowledgment: RSG and JLB gratefullya cknowledges upport of this work by the U.S. Public Health Service,N ational Institutes of Health, Grant No. HL 15104. Part of this work was conducted with the help of Dr. S. Steenken at the Max Planck Institut fir Strahlenchemie( Maheim), which E.A. thanks for its gracioush ospitality.

PY - 1992/3/24

Y1 - 1992/3/24

N2 - The selected dialkyl dithioethers 1,5-dithiocane, 1,4-dithiepane, 1,4-dithiane, and 2,6-dithiaheptane are readily monoalkylated in nitromethane by tert-butyl O-trifluoromethanesulfonyl-3-hydroxyperoxypropanoate, 6, to give the corresponding sulfonium salt peresters 2a-c, and 3 in good yield. Laser flash photolysis of these compounds affords the known two-sulfur, three-electron stabilized cation radicals 2a, b, and 5 which were characterized by optical absorption spectroscopy.

AB - The selected dialkyl dithioethers 1,5-dithiocane, 1,4-dithiepane, 1,4-dithiane, and 2,6-dithiaheptane are readily monoalkylated in nitromethane by tert-butyl O-trifluoromethanesulfonyl-3-hydroxyperoxypropanoate, 6, to give the corresponding sulfonium salt peresters 2a-c, and 3 in good yield. Laser flash photolysis of these compounds affords the known two-sulfur, three-electron stabilized cation radicals 2a, b, and 5 which were characterized by optical absorption spectroscopy.

KW - Sulfur-centered cation radical formation

KW - laser flash photolysis

KW - perester fragmentation

UR - https://www.scopus.com/pages/publications/0026511602

UR - https://www.scopus.com/pages/publications/0026511602#tab=citedBy

U2 - 10.1016/S0040-4039(00)91715-5

DO - 10.1016/S0040-4039(00)91715-5

M3 - Article

AN - SCOPUS:0026511602

SN - 0040-4039

VL - 33

SP - 1721

EP - 1724

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Formation of sulfur-centered cation radicals by photofragmentation

Abstract

Keywords

ASJC Scopus subject areas

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