Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to (Z)-1-diphenylphosphino-2-phenylsulfenylalkenes

R Alan Aitken; Graham Dawson; Neil Steven Keddie; Helmut Kraus; Alexandra Martha Zoya Slawin; Joanne Wheatley; J Derek Woollins

doi:10.1039/b913107h

Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to (Z)-1-diphenylphosphino-2-phenylsulfenylalkenes

R Alan Aitken, Graham Dawson, Neil Steven Keddie, Helmut Kraus, Alexandra Martha Zoya Slawin, Joanne Wheatley, J Derek Woollins

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

Abstract

While thermolysis of thiocarbonyl-stabilised phosphonium ylides generally results in extrusion of Ph3PS to give alkynes, those with a P=CH function instead undergo a novel P to S transfer of a phenyl group to give (Z)-configured 1-phosphino-2-sulfenyl-alkenes of interest as bidentate ligands.

Original language	English
Pages (from-to)	7381-7383
Number of pages	3
Journal	Chemical Communications
Volume	2009
Issue number	47
DOIs	https://doi.org/10.1039/b913107h
Publication status	Published - 2009

Keywords

FLASH VACUUM PYROLYSIS
PHOSPHORUS YLIDES
THIOCARBAMOYL ANALOGS
X-RAY
REACTIVITY
PHOSPHORYLATION
PENTACHLORIDE
KINETICS
ALKYNES

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10.1039/b913107h

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@article{3b1c35131f634ad9b7e4ba6ad368c434,

title = "Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to (Z)-1-diphenylphosphino-2-phenylsulfenylalkenes",

abstract = "While thermolysis of thiocarbonyl-stabilised phosphonium ylides generally results in extrusion of Ph3PS to give alkynes, those with a P=CH function instead undergo a novel P to S transfer of a phenyl group to give (Z)-configured 1-phosphino-2-sulfenyl-alkenes of interest as bidentate ligands.",

keywords = "FLASH VACUUM PYROLYSIS, PHOSPHORUS YLIDES, THIOCARBAMOYL ANALOGS, X-RAY, REACTIVITY, PHOSPHORYLATION, PENTACHLORIDE, KINETICS, ALKYNES",

author = "Aitken, {R Alan} and Graham Dawson and Keddie, {Neil Steven} and Helmut Kraus and Slawin, {Alexandra Martha Zoya} and Joanne Wheatley and Woollins, {J Derek}",

year = "2009",

doi = "10.1039/b913107h",

language = "English",

volume = "2009",

pages = "7381--7383",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "47",

}

TY - JOUR

T1 - Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to (Z)-1-diphenylphosphino-2-phenylsulfenylalkenes

AU - Aitken, R Alan

AU - Dawson, Graham

AU - Keddie, Neil Steven

AU - Kraus, Helmut

AU - Slawin, Alexandra Martha Zoya

AU - Wheatley, Joanne

AU - Woollins, J Derek

PY - 2009

Y1 - 2009

N2 - While thermolysis of thiocarbonyl-stabilised phosphonium ylides generally results in extrusion of Ph3PS to give alkynes, those with a P=CH function instead undergo a novel P to S transfer of a phenyl group to give (Z)-configured 1-phosphino-2-sulfenyl-alkenes of interest as bidentate ligands.

AB - While thermolysis of thiocarbonyl-stabilised phosphonium ylides generally results in extrusion of Ph3PS to give alkynes, those with a P=CH function instead undergo a novel P to S transfer of a phenyl group to give (Z)-configured 1-phosphino-2-sulfenyl-alkenes of interest as bidentate ligands.

KW - FLASH VACUUM PYROLYSIS

KW - PHOSPHORUS YLIDES

KW - THIOCARBAMOYL ANALOGS

KW - X-RAY

KW - REACTIVITY

KW - PHOSPHORYLATION

KW - PENTACHLORIDE

KW - KINETICS

KW - ALKYNES

U2 - 10.1039/b913107h

DO - 10.1039/b913107h

M3 - Article

SN - 1359-7345

VL - 2009

SP - 7381

EP - 7383

JO - Chemical Communications

JF - Chemical Communications

IS - 47

ER -

Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to (Z)-1-diphenylphosphino-2-phenylsulfenylalkenes

Abstract

Keywords

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