Desulfurization of aromatic polysulfides with triphenylphosphine

Eli Zysman-Colman; Patrick G. Farrell; David N. Harpp

doi:10.1080/1741599042000203364

Desulfurization of aromatic polysulfides with triphenylphosphine

Eli Zysman-Colman, Patrick G. Farrell, David N. Harpp^*

^*Corresponding author for this work

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

Abstract

The room temperature reaction of bis(4-methylbenzene) di- (3), tri- (4) and tetrasulfide (5) with triphenylphosphine has been followed by ¹H NMR. Mechanistic aspects of the cleavage of 3 and the desulfurization of 4 and 5, with concomitant formation of triphenylphosphine sulfide, are discussed. While tetrasulfide 5 is desulfurized over 10× faster than trisulfide 4, preliminary experiments indicate that 5 is not sufficiently reactive to efficiently transfer a sulfur atom to oligodeoxyribonucleotides.

Original language	English
Pages (from-to)	101-109
Number of pages	9
Journal	Journal of Sulfur Chemistry
Volume	25
Issue number	2-3
DOIs	https://doi.org/10.1080/1741599042000203364
Publication status	Published - 1 Apr 2004

Keywords

Desulfurization
Disulfides
Tetrasulfides
Triphenylphosphine
Trisulfides

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10.1080/1741599042000203364

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title = "Desulfurization of aromatic polysulfides with triphenylphosphine",

abstract = "The room temperature reaction of bis(4-methylbenzene) di- (3), tri- (4) and tetrasulfide (5) with triphenylphosphine has been followed by 1H NMR. Mechanistic aspects of the cleavage of 3 and the desulfurization of 4 and 5, with concomitant formation of triphenylphosphine sulfide, are discussed. While tetrasulfide 5 is desulfurized over 10× faster than trisulfide 4, preliminary experiments indicate that 5 is not sufficiently reactive to efficiently transfer a sulfur atom to oligodeoxyribonucleotides.",

keywords = "Desulfurization, Disulfides, Tetrasulfides, Triphenylphosphine, Trisulfides",

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T1 - Desulfurization of aromatic polysulfides with triphenylphosphine

AU - Zysman-Colman, Eli

AU - Farrell, Patrick G.

AU - Harpp, David N.

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Y1 - 2004/4/1

N2 - The room temperature reaction of bis(4-methylbenzene) di- (3), tri- (4) and tetrasulfide (5) with triphenylphosphine has been followed by 1H NMR. Mechanistic aspects of the cleavage of 3 and the desulfurization of 4 and 5, with concomitant formation of triphenylphosphine sulfide, are discussed. While tetrasulfide 5 is desulfurized over 10× faster than trisulfide 4, preliminary experiments indicate that 5 is not sufficiently reactive to efficiently transfer a sulfur atom to oligodeoxyribonucleotides.

AB - The room temperature reaction of bis(4-methylbenzene) di- (3), tri- (4) and tetrasulfide (5) with triphenylphosphine has been followed by 1H NMR. Mechanistic aspects of the cleavage of 3 and the desulfurization of 4 and 5, with concomitant formation of triphenylphosphine sulfide, are discussed. While tetrasulfide 5 is desulfurized over 10× faster than trisulfide 4, preliminary experiments indicate that 5 is not sufficiently reactive to efficiently transfer a sulfur atom to oligodeoxyribonucleotides.

KW - Desulfurization

KW - Disulfides

KW - Tetrasulfides

KW - Triphenylphosphine

KW - Trisulfides

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DO - 10.1080/1741599042000203364

M3 - Article

AN - SCOPUS:3142754857

SN - 1741-5993

VL - 25

SP - 101

EP - 109

JO - Journal of Sulfur Chemistry

JF - Journal of Sulfur Chemistry

IS - 2-3

ER -

Desulfurization of aromatic polysulfides with triphenylphosphine

Abstract

Keywords

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