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ホスフィン [化学構造分類] / Phosphines [Chemical Structural Class]

 リンは周期表において,窒素と同じ15族に属しており,炭素と結合し,種々の有機リン化合物を形成します。しかしながら,窒素は第2周期,リンは第3周期に属しているため,原子の大きさ,イオン化エネルギー,電気陰性度などが異なります。そのため,有機リン化合物は有機窒素化合物にない特徴的な反応性を示し,有機合成上有用な反応試剤として利用されています。例えば,リンは酸素に対する親和力が高く,リンイリド,ホスホナートはそれぞれWittig反応,Horner-Emmons反応に利用され,アルデヒドから酸素を引き抜き,オレフィンを生成します。ホスフィンは光延反応においてアルコールから酸素を引き抜き,エステルを生成させます。
このホスフィンのもう一つの大きな特徴として,ソフトな非共有電子対を有していることが挙げられます。そのため,パラジウムなどの遷移金属と比較的安定な錯体を形成します。この遷移金属錯体は鈴木―宮浦クロスカップリング反応,Heck反応などの触媒として多用されています1)。また,ホスフィンはアミンと同じく三角錐型の構造を取りますが,その反転障壁エネルギーは対応するアミンよりかなり大きな値を持ちます。3つの異なる置換基を持つホスフィンには光学異性体が存在します。この光学活性なホスフィンはP-キラル配位子として不斉合成に利用されています2)
B1112
(2S,3S)-(+)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol
B1137
1,2-Bis(diphenylphosphino)ethane
B1138
1,3-Bis(diphenylphosphino)propane
B1174
1,2-Bis(dimethylphosphino)ethane
B1246
1,4-Bis(diphenylphosphino)butane
B1405
(S)-(-)-BINAP
B1406
(R)-(+)-BINAP
B1959
1,6-Bis(diphenylphosphino)hexane
B1960
1,5-Bis(diphenylphosphino)pentane
B1982
Bis(diphenylphosphino)methane
B2003
trans-1,2-Bis(diphenylphosphino)ethylene
B2027
1,1'-Bis(diphenylphosphino)ferrocene
B2089
(S,S)-1,2-Bis[(tert-butyl)methylphosphino]ethane Bis(borane)
B2383
(±)-BINAP
B2630
2,2'-Bis(diphenylphosphino)biphenyl
B2704
(2S,3S)-(-)-Bis(diphenylphosphino)butane
B2709
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
B2710
1,1'-Bis(diisopropylphosphino)ferrocene
B2711
1,1'-Bis(di-tert-butylphosphino)ferrocene
B2717
4,6-Bis(diphenylphosphino)phenoxazine
B2867
Bis[2-(diphenylphosphino)phenyl] Ether
B3035
(R,R)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane
B3036
(S,S)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane
B3196
(R,R'')-2,2''-Bis(diphenylphosphino)-1,1''-biferrocene
B3428
1,2-Bis[bis(pentafluorophenyl)phosphino]ethane
B3449
(2R,3R)-(-)-2,3-Bis(diphenylphosphino)bicyclo[2.2.1]hept-5-ene
B3450
(2S,3S)-(+)-2,3-Bis(diphenylphosphino)bicyclo[2.2.1]hept-5-ene
B3953
(2-Bromophenyl)diphenylphosphine
B4272
1,1'-Bis(dichlorophosphino)ferrocene
B4530
1,8-Bis(diphenylphosphino)naphthalene
B4560
Bis(pentafluorophenyl)phenylphosphine
B4595
1,3-Bis[(di-tert-butylphosphino)oxy]benzene
B4644
2-Butenyl(di-tert-butyl)phosphine (cis- and trans- mixture)
B5239
4,5-Bis(dicyclohexylphosphino)-9,9-dimethylxanthene
B5301
(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
B5302
(S,S)-(+)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
B5712
Bis[2-(diisopropylphosphino)ethyl]amine (ca. 10% in Tetrahydrofuran)
C0597
Chlorodiphenylphosphine
C1429
Cyclohexyldiphenylphosphine
C2979
cBRIDP®
C2980
Cy-cBRIDP®
C2981
Cy-vBRIDP®
D1019
Diethylphenylphosphine
D2043
Sodium Diphenylphosphinobenzene-3-sulfonate
D2404
Diphenyl-1-pyrenylphosphine
D2411
Dicyclohexylphenylphosphine
D2471
Diphenyl-2-pyridylphosphine
D2478
4-(Dimethylamino)phenyldiphenylphosphine
D2535
(R)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine
D2536
(S)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine
D2537
(R)-N,N-Dimethyl-1-[(S)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine
D2538
(S)-N,N-Dimethyl-1-[(R)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine
D2630
Diphenylpropylphosphine
D2774
(R)-(+)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl
D3242
2-(Diphenylphosphino)benzoic Acid
D3243
4-(Diphenylphosphino)benzoic Acid
D3387
2-(Di-tert-butylphosphino)biphenyl
D3388
2-(Dicyclohexylphosphino)biphenyl
D3389
2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl
D3834
1-[2-(Di-tert-butylphosphino)phenyl]-3,5-diphenyl-1H-pyrazole
D3940
Di-tert-butylphenylphosphine
D4411
2-(Diphenylphosphino)benzaldehyde
D4498
(S)-(-)-DM-SEGPHOS®
D4499
(R)-(+)-DM-SEGPHOS®
D4500
(S)-(+)-DTBM-SEGPHOS®
D4501
(R)-(-)-DTBM-SEGPHOS®
D4531
(4-Dimethylaminophenyl)di-tert-butylphosphine
D4686
Di-tert-butyl(3-methyl-2-butenyl)phosphine
D4688
2-(Diphenylphosphino)biphenyl
D4781
Di-1-adamantylphosphine
D4825
3-(Diphenylphosphino)-1-propylamine
D4953
2-(Diphenylphosphino)benzonitrile
D5035
2-Dicyclohexylphosphino-2'-methylbiphenyl
D5036
2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
D5037
2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl
D5038
2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl
D5039
2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl
D5663
Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine
D5664
Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine
E0519
Ethyldiphenylphosphine
I0583
Isopropyldiphenylphosphine
M1318
Methyldiphenylphosphine
M2103
1-Methyl-1-[4-(diphenylphosphino)benzyl]pyrrolidinium Bromide
P1176
(Pentafluorophenyl)diphenylphosphine
S0929
(S)-(-)-SEGPHOS®
S0930
(R)-(+)-SEGPHOS®
T0361
Tributylphosphine
T0503
Tri-n-octylphosphine
T0519
Triphenylphosphine
T0861
Tris(4-methoxyphenyl)phosphine
T0862
Tri(p-tolyl)phosphine
T1005
Trihexylphosphine
T1024
Tri(o-tolyl)phosphine
T1025
Tri(m-tolyl)phosphine
T1165
Tricyclohexylphosphine (contains Tricyclohexylphosphine Oxide) (ca. 18% in Toluene, ca. 0.60mol/L)
T1614
Tris(2,6-dimethoxyphenyl)phosphine
T1643
Tri(2-furyl)phosphine
T1656
Tris(2-carboxyethyl)phosphine Hydrochloride
T1666
Tri(2-thienyl)phosphine
T1757
Triphenylborane - Triphenylphosphine Complex
T1789
Triphenylphosphine Borane
T1912
Tri-tert-butylphosphine
T2248
Tricyclopentylphosphine
T2484
Tris(pentafluorophenyl)phosphine
T2526
Tris[3,5-bis(trifluoromethyl)phenyl]phosphine
T2900
Tris(4-fluorophenyl)phosphine
T3005
Tris(2-methoxyphenyl)phosphine
T3152
(R)-(+)-TolBINAP
T3153
(S)-(-)-TolBINAP
T3489
Trimethylphosphine
V0132
vBRIDP®
X0070
(R)-(+)-XylBINAP
X0071
(S)-(-)-XylBINAP

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