Secondary diphosphine and diphosphido ligands: synthesis, characterisation and group 1 coordination compounds
Two types of secondary diphosphines, 1,8-(ArPH) 2 C 14 H 8 ( 1a : Ar = Tripp, 2,4,6-triisopropylphenyl; 1b : Ar = Mes, 2,4,6-trimethylphenyl) and 1,3-( t BuPHCH 2 ) 2 C 6 H 4 ( 2 ), based on rigid 1,8-anthracene and flexible m -xylyl frameworks, respectively, have been synthesized using different st...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2014-01, Vol.43 (1), p.267-276 |
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| creator | Ritch, Jamie S Julienne, Delphine Rybchinski, Shayne R Brockman, Kathryne S Johnson, Kevin R. D Hayes, Paul G |
| description | Two types of secondary diphosphines, 1,8-(ArPH)
2
C
14
H
8
(
1a
: Ar = Tripp, 2,4,6-triisopropylphenyl;
1b
: Ar = Mes, 2,4,6-trimethylphenyl) and 1,3-(
t
BuPHCH
2
)
2
C
6
H
4
(
2
), based on rigid 1,8-anthracene and flexible
m
-xylyl frameworks, respectively, have been synthesized using different strategies. Compounds
1a
and
1b
were formed by nucleophilic aromatic substitution of a potassium organophosphido salt onto 1,8-difluoroanthracene, while compound
2
was obtained by addition of the Grignard reagent [1,3-(ClMgCH
2
)
2
C
6
H
4
]
x
to a dichloroorganophosphine, followed by reduction to the diphosphine. These compounds were isolated as
ca
. 1 : 1 mixtures of
rac
and
meso
diastereomers as determined by multinuclear NMR spectroscopy. Borane and selenide derivatives of
2
, 1,3-(
t
BuPH(BH
3
)CH
2
)
2
C
6
H
4
(
3
) and 1,3-(
t
BuPH(Se)CH
2
)
2
C
6
H
4
(
4
), were obtained. Preferential crystallization of one diastereomer of
3
and
4
was observed; X-ray crystallographic studies identified this as the
rac
isomer for diselenide
4
. Metallation studies of compounds
1a
and
2
yielded several alkali metal salts. The reaction of KH or K metal with
1a
yielded the compounds 1,8-(TrippPK)
2
C
14
H
8
·
x
THF (
5
) and 1,8-(TrippPK)
2
C
14
H
10
·
x
THF (
6
), respectively; in complex
6
the central aromatic ring has been reduced to yield a bent dihydroanthracene backbone. A crown ether derivative of
6
, [K(18-crown-6)(THF)
2
]
2
[1,8-(TrippP)
2
C
14
H
10
] (
7
), was characterised crystallographically. Double deprotonation of compound
2
with
n
BuLi/TMEDA (TMEDA =
N
,
N
,
N
′,
N
′-tetramethylethylenediamine) afforded the yellow dilithium complex 1,3-(
t
BuPLiCH
2
)
2
C
6
H
4
·TMEDA (
8
), which crystallized as a dimer featuring lithium-arene π interactions.
Two new secondary phosphines have been prepared as 1 : 1 mixtures of
rac
/
meso
diastereomers. They undergo reactions with group 1 reagents to cleanly afford unusual diphosphido complexes. |
| doi_str_mv | 10.1039/c3dt51844b |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_rsc_primary_c3dt51844b</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1462370598</sourcerecordid><originalsourceid>FETCH-LOGICAL-c309t-77fd04b5fb29f19328b6ae343bef30dc30d5f8e6d6113a544184676d074720843</originalsourceid><addsrcrecordid>eNpFkTtPwzAUhS0EoqWwsIM8IkTAr8QJG5SnVImBMkeO7TRGSRzsZOi_xzSlne7ru0e65wJwjtEtRjS7k1T1MU4ZKw7AFDPOo4xQdrjLSTIBJ95_I0QIiskxmBCGEUMxn4LmU0vbKuHWUJmusr6rTKuhaNW-VhbWZhVa_h76ddtX2ht_A2UlnJC9dsaL3th2s7RydugghtJap0w7DqRtOjuE_VNwVIra67NtnIGvl-fl_C1afLy-zx8WkaQo6yPOS4VYEZcFyUqcUZIWidCU0UKXFKkAqbhMdaISjKmIGQvHJzxRiDNOUMroDFyNup2zP4P2fd4YL3Vdi1bbweeYJYRyFGdpQK9HVDrrvdNl3jnTBD9yjPI_e_M5fVpu7H0M8OVWdygarXbov58BuBgB5-Vuuv8P_QVKd4B6</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1462370598</pqid></control><display><type>article</type><title>Secondary diphosphine and diphosphido ligands: synthesis, characterisation and group 1 coordination compounds</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Ritch, Jamie S ; Julienne, Delphine ; Rybchinski, Shayne R ; Brockman, Kathryne S ; Johnson, Kevin R. D ; Hayes, Paul G</creator><creatorcontrib>Ritch, Jamie S ; Julienne, Delphine ; Rybchinski, Shayne R ; Brockman, Kathryne S ; Johnson, Kevin R. D ; Hayes, Paul G</creatorcontrib><description>Two types of secondary diphosphines, 1,8-(ArPH)
2
C
14
H
8
(
1a
: Ar = Tripp, 2,4,6-triisopropylphenyl;
1b
: Ar = Mes, 2,4,6-trimethylphenyl) and 1,3-(
t
BuPHCH
2
)
2
C
6
H
4
(
2
), based on rigid 1,8-anthracene and flexible
m
-xylyl frameworks, respectively, have been synthesized using different strategies. Compounds
1a
and
1b
were formed by nucleophilic aromatic substitution of a potassium organophosphido salt onto 1,8-difluoroanthracene, while compound
2
was obtained by addition of the Grignard reagent [1,3-(ClMgCH
2
)
2
C
6
H
4
]
x
to a dichloroorganophosphine, followed by reduction to the diphosphine. These compounds were isolated as
ca
. 1 : 1 mixtures of
rac
and
meso
diastereomers as determined by multinuclear NMR spectroscopy. Borane and selenide derivatives of
2
, 1,3-(
t
BuPH(BH
3
)CH
2
)
2
C
6
H
4
(
3
) and 1,3-(
t
BuPH(Se)CH
2
)
2
C
6
H
4
(
4
), were obtained. Preferential crystallization of one diastereomer of
3
and
4
was observed; X-ray crystallographic studies identified this as the
rac
isomer for diselenide
4
. Metallation studies of compounds
1a
and
2
yielded several alkali metal salts. The reaction of KH or K metal with
1a
yielded the compounds 1,8-(TrippPK)
2
C
14
H
8
·
x
THF (
5
) and 1,8-(TrippPK)
2
C
14
H
10
·
x
THF (
6
), respectively; in complex
6
the central aromatic ring has been reduced to yield a bent dihydroanthracene backbone. A crown ether derivative of
6
, [K(18-crown-6)(THF)
2
]
2
[1,8-(TrippP)
2
C
14
H
10
] (
7
), was characterised crystallographically. Double deprotonation of compound
2
with
n
BuLi/TMEDA (TMEDA =
N
,
N
,
N
′,
N
′-tetramethylethylenediamine) afforded the yellow dilithium complex 1,3-(
t
BuPLiCH
2
)
2
C
6
H
4
·TMEDA (
8
), which crystallized as a dimer featuring lithium-arene π interactions.
Two new secondary phosphines have been prepared as 1 : 1 mixtures of
rac
/
meso
diastereomers. They undergo reactions with group 1 reagents to cleanly afford unusual diphosphido complexes.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c3dt51844b</identifier><identifier>PMID: 24104057</identifier><language>eng</language><publisher>England</publisher><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2014-01, Vol.43 (1), p.267-276</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c309t-77fd04b5fb29f19328b6ae343bef30dc30d5f8e6d6113a544184676d074720843</citedby><cites>FETCH-LOGICAL-c309t-77fd04b5fb29f19328b6ae343bef30dc30d5f8e6d6113a544184676d074720843</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24104057$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ritch, Jamie S</creatorcontrib><creatorcontrib>Julienne, Delphine</creatorcontrib><creatorcontrib>Rybchinski, Shayne R</creatorcontrib><creatorcontrib>Brockman, Kathryne S</creatorcontrib><creatorcontrib>Johnson, Kevin R. D</creatorcontrib><creatorcontrib>Hayes, Paul G</creatorcontrib><title>Secondary diphosphine and diphosphido ligands: synthesis, characterisation and group 1 coordination compounds</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Two types of secondary diphosphines, 1,8-(ArPH)
2
C
14
H
8
(
1a
: Ar = Tripp, 2,4,6-triisopropylphenyl;
1b
: Ar = Mes, 2,4,6-trimethylphenyl) and 1,3-(
t
BuPHCH
2
)
2
C
6
H
4
(
2
), based on rigid 1,8-anthracene and flexible
m
-xylyl frameworks, respectively, have been synthesized using different strategies. Compounds
1a
and
1b
were formed by nucleophilic aromatic substitution of a potassium organophosphido salt onto 1,8-difluoroanthracene, while compound
2
was obtained by addition of the Grignard reagent [1,3-(ClMgCH
2
)
2
C
6
H
4
]
x
to a dichloroorganophosphine, followed by reduction to the diphosphine. These compounds were isolated as
ca
. 1 : 1 mixtures of
rac
and
meso
diastereomers as determined by multinuclear NMR spectroscopy. Borane and selenide derivatives of
2
, 1,3-(
t
BuPH(BH
3
)CH
2
)
2
C
6
H
4
(
3
) and 1,3-(
t
BuPH(Se)CH
2
)
2
C
6
H
4
(
4
), were obtained. Preferential crystallization of one diastereomer of
3
and
4
was observed; X-ray crystallographic studies identified this as the
rac
isomer for diselenide
4
. Metallation studies of compounds
1a
and
2
yielded several alkali metal salts. The reaction of KH or K metal with
1a
yielded the compounds 1,8-(TrippPK)
2
C
14
H
8
·
x
THF (
5
) and 1,8-(TrippPK)
2
C
14
H
10
·
x
THF (
6
), respectively; in complex
6
the central aromatic ring has been reduced to yield a bent dihydroanthracene backbone. A crown ether derivative of
6
, [K(18-crown-6)(THF)
2
]
2
[1,8-(TrippP)
2
C
14
H
10
] (
7
), was characterised crystallographically. Double deprotonation of compound
2
with
n
BuLi/TMEDA (TMEDA =
N
,
N
,
N
′,
N
′-tetramethylethylenediamine) afforded the yellow dilithium complex 1,3-(
t
BuPLiCH
2
)
2
C
6
H
4
·TMEDA (
8
), which crystallized as a dimer featuring lithium-arene π interactions.
Two new secondary phosphines have been prepared as 1 : 1 mixtures of
rac
/
meso
diastereomers. They undergo reactions with group 1 reagents to cleanly afford unusual diphosphido complexes.</description><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpFkTtPwzAUhS0EoqWwsIM8IkTAr8QJG5SnVImBMkeO7TRGSRzsZOi_xzSlne7ru0e65wJwjtEtRjS7k1T1MU4ZKw7AFDPOo4xQdrjLSTIBJ95_I0QIiskxmBCGEUMxn4LmU0vbKuHWUJmusr6rTKuhaNW-VhbWZhVa_h76ddtX2ht_A2UlnJC9dsaL3th2s7RydugghtJap0w7DqRtOjuE_VNwVIra67NtnIGvl-fl_C1afLy-zx8WkaQo6yPOS4VYEZcFyUqcUZIWidCU0UKXFKkAqbhMdaISjKmIGQvHJzxRiDNOUMroDFyNup2zP4P2fd4YL3Vdi1bbweeYJYRyFGdpQK9HVDrrvdNl3jnTBD9yjPI_e_M5fVpu7H0M8OVWdygarXbov58BuBgB5-Vuuv8P_QVKd4B6</recordid><startdate>20140107</startdate><enddate>20140107</enddate><creator>Ritch, Jamie S</creator><creator>Julienne, Delphine</creator><creator>Rybchinski, Shayne R</creator><creator>Brockman, Kathryne S</creator><creator>Johnson, Kevin R. D</creator><creator>Hayes, Paul G</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20140107</creationdate><title>Secondary diphosphine and diphosphido ligands: synthesis, characterisation and group 1 coordination compounds</title><author>Ritch, Jamie S ; Julienne, Delphine ; Rybchinski, Shayne R ; Brockman, Kathryne S ; Johnson, Kevin R. D ; Hayes, Paul G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c309t-77fd04b5fb29f19328b6ae343bef30dc30d5f8e6d6113a544184676d074720843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ritch, Jamie S</creatorcontrib><creatorcontrib>Julienne, Delphine</creatorcontrib><creatorcontrib>Rybchinski, Shayne R</creatorcontrib><creatorcontrib>Brockman, Kathryne S</creatorcontrib><creatorcontrib>Johnson, Kevin R. D</creatorcontrib><creatorcontrib>Hayes, Paul G</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ritch, Jamie S</au><au>Julienne, Delphine</au><au>Rybchinski, Shayne R</au><au>Brockman, Kathryne S</au><au>Johnson, Kevin R. D</au><au>Hayes, Paul G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Secondary diphosphine and diphosphido ligands: synthesis, characterisation and group 1 coordination compounds</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2014-01-07</date><risdate>2014</risdate><volume>43</volume><issue>1</issue><spage>267</spage><epage>276</epage><pages>267-276</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Two types of secondary diphosphines, 1,8-(ArPH)
2
C
14
H
8
(
1a
: Ar = Tripp, 2,4,6-triisopropylphenyl;
1b
: Ar = Mes, 2,4,6-trimethylphenyl) and 1,3-(
t
BuPHCH
2
)
2
C
6
H
4
(
2
), based on rigid 1,8-anthracene and flexible
m
-xylyl frameworks, respectively, have been synthesized using different strategies. Compounds
1a
and
1b
were formed by nucleophilic aromatic substitution of a potassium organophosphido salt onto 1,8-difluoroanthracene, while compound
2
was obtained by addition of the Grignard reagent [1,3-(ClMgCH
2
)
2
C
6
H
4
]
x
to a dichloroorganophosphine, followed by reduction to the diphosphine. These compounds were isolated as
ca
. 1 : 1 mixtures of
rac
and
meso
diastereomers as determined by multinuclear NMR spectroscopy. Borane and selenide derivatives of
2
, 1,3-(
t
BuPH(BH
3
)CH
2
)
2
C
6
H
4
(
3
) and 1,3-(
t
BuPH(Se)CH
2
)
2
C
6
H
4
(
4
), were obtained. Preferential crystallization of one diastereomer of
3
and
4
was observed; X-ray crystallographic studies identified this as the
rac
isomer for diselenide
4
. Metallation studies of compounds
1a
and
2
yielded several alkali metal salts. The reaction of KH or K metal with
1a
yielded the compounds 1,8-(TrippPK)
2
C
14
H
8
·
x
THF (
5
) and 1,8-(TrippPK)
2
C
14
H
10
·
x
THF (
6
), respectively; in complex
6
the central aromatic ring has been reduced to yield a bent dihydroanthracene backbone. A crown ether derivative of
6
, [K(18-crown-6)(THF)
2
]
2
[1,8-(TrippP)
2
C
14
H
10
] (
7
), was characterised crystallographically. Double deprotonation of compound
2
with
n
BuLi/TMEDA (TMEDA =
N
,
N
,
N
′,
N
′-tetramethylethylenediamine) afforded the yellow dilithium complex 1,3-(
t
BuPLiCH
2
)
2
C
6
H
4
·TMEDA (
8
), which crystallized as a dimer featuring lithium-arene π interactions.
Two new secondary phosphines have been prepared as 1 : 1 mixtures of
rac
/
meso
diastereomers. They undergo reactions with group 1 reagents to cleanly afford unusual diphosphido complexes.</abstract><cop>England</cop><pmid>24104057</pmid><doi>10.1039/c3dt51844b</doi><tpages>1</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2014-01, Vol.43 (1), p.267-276 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_rsc_primary_c3dt51844b |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Secondary diphosphine and diphosphido ligands: synthesis, characterisation and group 1 coordination compounds |
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