Fluorinated Phosphorus-Selenium Heteroatom Compounds: Phenylphosphonofluorodiselenoic Salts, Adducts, and Esters

Guoxiong Hua; Junyi Du; Alexandra M. Z. Slawin; J. Derek Woollins

doi:10.1021/ic400612w

Fluorinated Phosphorus-Selenium Heteroatom Compounds: Phenylphosphonofluorodiselenoic Salts, Adducts, and Esters

Guoxiong Hua, Junyi Du, Alexandra M. Z. Slawin, J. Derek Woollins^*

^*Corresponding author for this work

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

Abstract

2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide, [PhP(Se)(mu-Se)](2), Woollins' reagent (WR), reacts with dry KF or tetrabutylammonium fluoride (TBAF) at room temperature generating the corresponding potassium and tetrabutylammonium phenyldiselenofluorophosphinates 1 and 2 in almost quantitative yields. Treating 1 with equimolar amounts of tetraphenylphosphonium chloride or 1,3-dimesityl-1H-imidazol-3-ium chloride in THF at room temperature afforded the corresponding organic adducts 3 and 4 in 90% and 87% yields. Reaction of 1 with mono- and dihalogenated alkanes gave a series of esters of phenylphosphonofluoridodiselenoates 5-8 and 9 in 79-93% yields. Two representative crystal structures are reported.

Original language	English
Pages (from-to)	8214-8217
Number of pages	4
Journal	Inorganic Chemistry
Volume	52
Issue number	14
Early online date	1 Jul 2013
DOIs	https://doi.org/10.1021/ic400612w
Publication status	Published - 15 Jul 2013

Keywords

Woollins' reagent
Efficient synthesis
Analogs
Heterocycles
Acetylcholinesterase
Phosphorofluoridate
Selenation

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10.1021/ic400612w

Inorg_Chem2013
© 2013, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Inorganic Chemistry after peer review and technical editing by the publisher. To access the final edited and published work see DOI: 10.1021/ic400612w
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@article{debe8acdbc904af48c96fe3dda11d592,

title = "Fluorinated Phosphorus-Selenium Heteroatom Compounds: Phenylphosphonofluorodiselenoic Salts, Adducts, and Esters",

abstract = "2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide, [PhP(Se)(mu-Se)](2), Woollins' reagent (WR), reacts with dry KF or tetrabutylammonium fluoride (TBAF) at room temperature generating the corresponding potassium and tetrabutylammonium phenyldiselenofluorophosphinates 1 and 2 in almost quantitative yields. Treating 1 with equimolar amounts of tetraphenylphosphonium chloride or 1,3-dimesityl-1H-imidazol-3-ium chloride in THF at room temperature afforded the corresponding organic adducts 3 and 4 in 90\% and 87\% yields. Reaction of 1 with mono- and dihalogenated alkanes gave a series of esters of phenylphosphonofluoridodiselenoates 5-8 and 9 in 79-93\% yields. Two representative crystal structures are reported.",

keywords = "Woollins' reagent, Efficient synthesis, Analogs, Heterocycles, Acetylcholinesterase, Phosphorofluoridate , Selenation",

author = "Guoxiong Hua and Junyi Du and Slawin, \{Alexandra M. Z.\} and Woollins, \{J. Derek\}",

year = "2013",

month = jul,

day = "15",

doi = "10.1021/ic400612w",

language = "English",

volume = "52",

pages = "8214--8217",

journal = "Inorganic Chemistry",

issn = "0020-1669",

publisher = "American Chemical Society (ACS)",

number = "14",

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TY - JOUR

T1 - Fluorinated Phosphorus-Selenium Heteroatom Compounds

T2 - Phenylphosphonofluorodiselenoic Salts, Adducts, and Esters

AU - Hua, Guoxiong

AU - Du, Junyi

AU - Slawin, Alexandra M. Z.

AU - Woollins, J. Derek

PY - 2013/7/15

Y1 - 2013/7/15

N2 - 2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide, [PhP(Se)(mu-Se)](2), Woollins' reagent (WR), reacts with dry KF or tetrabutylammonium fluoride (TBAF) at room temperature generating the corresponding potassium and tetrabutylammonium phenyldiselenofluorophosphinates 1 and 2 in almost quantitative yields. Treating 1 with equimolar amounts of tetraphenylphosphonium chloride or 1,3-dimesityl-1H-imidazol-3-ium chloride in THF at room temperature afforded the corresponding organic adducts 3 and 4 in 90% and 87% yields. Reaction of 1 with mono- and dihalogenated alkanes gave a series of esters of phenylphosphonofluoridodiselenoates 5-8 and 9 in 79-93% yields. Two representative crystal structures are reported.

AB - 2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide, [PhP(Se)(mu-Se)](2), Woollins' reagent (WR), reacts with dry KF or tetrabutylammonium fluoride (TBAF) at room temperature generating the corresponding potassium and tetrabutylammonium phenyldiselenofluorophosphinates 1 and 2 in almost quantitative yields. Treating 1 with equimolar amounts of tetraphenylphosphonium chloride or 1,3-dimesityl-1H-imidazol-3-ium chloride in THF at room temperature afforded the corresponding organic adducts 3 and 4 in 90% and 87% yields. Reaction of 1 with mono- and dihalogenated alkanes gave a series of esters of phenylphosphonofluoridodiselenoates 5-8 and 9 in 79-93% yields. Two representative crystal structures are reported.

KW - Woollins' reagent

KW - Efficient synthesis

KW - Analogs

KW - Heterocycles

KW - Acetylcholinesterase

KW - Phosphorofluoridate

KW - Selenation

UR - https://www.scopus.com/pages/publications/84880255568

U2 - 10.1021/ic400612w

DO - 10.1021/ic400612w

M3 - Article

SN - 0020-1669

VL - 52

SP - 8214

EP - 8217

JO - Inorganic Chemistry

JF - Inorganic Chemistry

IS - 14

ER -

Fluorinated Phosphorus-Selenium Heteroatom Compounds: Phenylphosphonofluorodiselenoic Salts, Adducts, and Esters

Abstract

Keywords

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