3 Phosphine Oxides and Related Compounds

BY B. J. WALKER

1 Introduction

This has been a year of consolidation. although interest in low-

coordinate phosphorus and in phosphine oxide-based olefin synthesis

continues to grow. I thank those who have correctly suggested that

I point out that the coverage in Section 7 (Phosphine Oxide

Complexes and Extractants) is much more selective and less

comprehensive than that in other sections in this Chapter.

2 Preparation of Acyclic Phosphine Oxides

Cyclopropyldiphenylphosphine oxides ( e 2 . 1) have been prepared by

reaction of m-dibromocyclopropanes with diphenylphosphide followed

by oxidation.' The report includes a discussion of the mechanism of

the substitution reaction. A new route to optically active tertiary

methylphenylphosphine oxides which contain a sterically bulky group

has been reported.'

secondary phosphine oxide with (-)-menthylchloroacetate followed by

resolution by crystallization, hydrolysis, and decarboxylation

(Scheme 1). In cases where they were determined, the optical

purities of the products were high ( 2 95% e.e.) and the overall

yields of each isomer Varied from 8% to 38%.

The method involves reaction of the appropriate

(2-_N-Substituted pyrrolidy1)diphenylphosphine oxides (2) are

readily prepared by reaction of chlorodiphenylphosphine with

- N-substituted tetrahydro-1,3-oxazines followed by base treatment.

Reactions of the carbanions of (2) with aldehydes OK

3

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82 Organophosphorus Chemisfry

ketones provide a route to heterocyclic enamines and,

acid-catalysed rearrangement, enamides (Scheme 2).

A convenient synthesis of certain 2-substitutedphenyl(dipheny1)-

phosphineoxides (3) via o-lithiation of triphenylphosphine oxide has

been briefly reported. Nucleophilic aromatic substitution of

fluorophenylphosphine oxides has been used to prepare a variety of

triarylphosphine oxides ( 4 ) and hence the corresponding

phosphines. The W-visible spectra of these compounds are

discussed and comparisons are made with the corresponding amines.

(Halogenophenoxymethy1)phosphine oxides ( 5 ) 6 and cyclic (e3. 6 ) and

acyclic (e.g. 7) alkoxymethylphosphine oxides7 have been obtained

from the reaction of bis- and tris(chloromethy1)phosphine oxides

with halogenophenoxide anions and 1.2-diols, respectively.

An efficient one-pot synthesis of cyclohex-3-enylphosphine

oxides (8) is available by a multiple Michael addition and

ring-closure procedure (Scheme 3 ) .' be prepared' by the reaction of g-chloroylides with aldehydes or

ketones (see also Chapter 8). A new route to diphenylvinylphosphine

oxides (10) involves deoxygenation of the appropriate

1,2-epoxyethylphosphine oxide with diphosphorus tetraiodide as the

key step."

Vinylphosphine oxides (9) can

The interest in p,-bonded phosphorus continues to grow in all

areas of phosphorus chemistry. Tricoordinate phosphorus oxides,

sulphides,and selenides have been prepared by reactions of

phosphaalkene (11) with, respectively, ozone, sulphur,and

selenium. l1

sulphide (12) generates the methylenephosphine sulphide (13) as

evidenced by trapping with methanol, 2,3-dimethylbut-1,3-diene,and

benzylideneacetophenone (Scheme 4 ) . l2

[4+21 addition to the butadiene since Diels-Alder reactions are

unknown for methylenephosphine oxides (14). The first example of a

Thermal decomposition of the bicyclic phosphorus

Especially interesting is the

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3: Phosphine Oxides and Related Compounds 83

PhP(0)H + CICH,COOR2 - PhP(0)CH2COOR2 I R'

I R'

1 0 II I

R1

P h -P -CH 2CO0 Rf

ii, iii 1 0

i, ii f

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84 Organophosphorus Chemistry

Ph2P(0)

6" ( 3 ) R = Me, CH(0H) Me, or COOH (4) R = CSHloN or NOz, n = 1 , 2 , or 3

0 II , CH,OC H,

\CH,OCH, HOCHRCHZOCH P i

3 - n

0 II

MeP( CH,OCHMeOH Iz

Scheme 3

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3: Phosphine Oxides and Related Compounds 85

X - 0 , s . or S.

Ph

S 4 'Ph

Reagents: i, x C E C X ; ii. P4Sm;iii, Me, A , toluene X M .

M+x ' x Ph

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86 Organophosphorus Chemistry

stable metadithiophosphonate (15) has been prepared by reaction of

tris(tertiary buty1)phenylphosphine with sulphur to give the

corresponding sulphide,which on further reaction gives

bis[tris(tertiary butyl)phenyl]trithiodiphosphinate and finally

(15) - 13

Both l-(diphenylthiophosphoryl)-~-alkylthioformimidates (16)

and their 2-methyl derivatives (17) have been prepared from the

corresponding phosphines and shown, by n.m.r. spectroscopy, to exist

as E/Z mixtures with the Z-conf iguration predominating."

3 Preparation of Cyclic Phosphine Oxides

A new entry into the hydrophosphindole ring system has been

reported.15

of the readily available a-terpinene into (18). The easily

prepared 3-phospholene oxides (19) are converted by ozonolysis into

bis(B-oxoalky1)phosphine oxides, which in turn undergo aldol

condensation when treated with p-toluenesulphonic acid to provide a

new synthesis of phosphorinones (20) (Scheme 5). Phosphacarnegine

(23) has been prepared in low yield by two long routes derived by

use of the computer-aided synthesis program PASCOP and involving

cyclization of the phosphine oxide (21) and phosphinate (22) as key

steps.17 One point of interest is the methylation of the phosphine

oxide (24). which gives primarily one diastereomer, but also the

dimethylated product (25).

The method is not general since it involves conversion

Using his previously published route to nine-membered

phosphorus-containing rings ( e A . 26) as a starting point, Quin has

succeeded in synthesizing the first all-& monocyclic phosphonin

oxide (27) (Scheme 6):'

accomplished in a step-wise fashion and the formation of (27) is

accompanied by equal amounts of the Fc'-phosphorin (28).

structural assignments are supported by extensive n.m.r. data and a

The two dehydrohalogenations can be

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3: Phosphine Oxides and Related Compounds

S 5 s

87

SO 11 s II I I 0 s H H *S

ArPHt - ArPH, ArPSPAr ArP’

PhtP( S) C ( S) NH R Ph,P( S) C=NR I

MeS

(16) (17)

(1 9) (20)

Reagents: i, 03; ii. (Mc0)3P; iii, $” Scheme 5

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88 Organop h osp h orus Chemistry

(21)

M e 0 W P M e \

Me

( 2 4 ) Me -Me

Br Br Br Br

0

Ph’ %O

( 2 6 ) J ii

MeJSiO 0 \ 1 OSiMe, + Me3 S i O q

/ \ Ph’ \o Me3Si0 Ph 0

Reagents: i , Me3SiX; ii. 2 x EtJN

S c h e m e 6

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3: Phosphine Oxides and Related Compounds 89

reasonable mechanism is proposed for the formation of (28).

4 Structure and Physical Aspects

The electronic structure of the phosphoryl and thiophosphoryl bonds

has been investigated on a STO-ZG* and 6-31G* basis.” The results

indicate a significant contribution from triply bonded PO structures

and in some cases the PO bond order approaches that of a double

bond. Ab initio calculations of the isomerization reaction of

diphosphene 1-sulphide (29) to thiadiphosphirane (30) have been

reported.”

kcal mol-I less stable than (30).

The results suggest that in the ground state (29) is 21

There has been some recent interest in the structure of

2-[1,3]dithianyldiphenylphosphine oxide (31). not least because it

adopts a predominantly axial configuration in spite of the absence

of lone pairs on phosphorus.’l

4.6-dimethyl derivative ( 3 3 ) . where the equatorial conformation must

predominate, has now been carried out.”

parameters obtained for (33) with those of (31) argues against

contributions from n * aC-p interactions. i?. (32).

An X-ray structure of the

A comparison of the bond

* -E

(~)-(-)-~-(3,5-Dinitrobenzoyl)-a-phenylethylamine (34) is

reported to give good enantiomeric differentiation in the n.m.r.

spectra of chiral phosphine oxides, both where the chirality is at

phosphorus and where it is at the a-carbon atom.23

also be applied to chiral phosphines by in situ stereospecific

oxidation with tertiary butyl hydroperoxide.

The reagent can

5 Reactions at Phosphorus

The reduction of a number of bridged cyclic phosphine oxides with

silanes has been in~estigated.’~

chemistry of reduction in some cases when compared to reductions of

nun-cyclic phosphine oxides are attributed to the involvement of

Differences in the stereo-

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Organophosphorus Chemistry

ArP=PAr II S

(29 1

- ArP-PAr

'4 ( 3 0 )

Reagents: i, HSiCL3: i i , HSiCI3, p y r i d i n c

Schema 1

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3: Phosphine Oxides and Related Compounds 91

pentacoordinated intermediates. However, the stereochemistry of

reductions in the presence of pyridine is not affected and a

different mechanism is thought to operate in these cases. In

reductions of phosphole oxide dimers (e.g. 35). loss of the

phosphorus bridge to give (36) can predominate, although simple

reduction to the phosphole dimer (37) can be accomplished by using

the silane-pyridine method (Scheme 7).

-

The phosphine sulphide (39). obtained by reaction of the highly

reactive phosphorin sulphide ( 3 8 ) with 2.3-dimethylbutadiene, has

been converted by a series of reactions into 3.4-dimethylphosphorin

(40) (Scheme 8). 25

6 Reactions at the Side-chain

Several examples of the use of vinylphosphine oxides as

dipolarophiles have been reported. Phosphindole oxides (41) react

regio- and stereospecifically with diphenylnitrilimine to give the

expected adduct (42). 26 Cyclobutenyldiphenylphosphine oxide (43)

and the corresponding phosphonium salt undergo a similar reaction

with 1.3-dipoles to give a variety of heterocyclic substituted

phosphine oxides (Scheme 9) and phosphonium salts .27

Michael additions to vinylphosphine oxides continue to be

investigated. Horner has shown that diphenylvinylphosphine oxide

reacts selectively with -SH in the presence of -OH groups; however,

the rate of reaction is too slow to provide a worthwhile SH

protecting reagent. 28

(44). (45),and (46) have been prepared directly from

allenylphosphine oxides by similar types of reactions (Scheme

A variety of f3-functionalized derivatives

10). 29

The Michael addition of carbanions derived from

allylic phosphine oxides to cyclic enones gives vinylphosphine oxides

(u. 47) as single diastereomers. 30 A ten-membered "chair-chairn-

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92

Me

Organophosphorus Chemistry

Me Me

(38 1 (39) III , i v I ...

Me I

Me

S Ph

lv

(40) Ph

Reagents: i , M e ; i i , 2 0 , 2 CF3COOH, CH2C12 ; i i i , 5 X C 3 C X , 1 O O ' C ;

X M e

i v , p4SW; v, ZBu3P, 150 'C

S c h e m e 8

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3: Phosphine Oxides and Related Compounds 93

P hz Pg0

b ( 4 3 )

ii iii > - - - c

PhzP=O PhzP = 0

PhZP SR =O

+ - Ph, +A- Reagents: i , CH2F+; ii. BuLi ; i i i .Me1; i v , RCEN-0 ; v , C=N

H’ ‘Ph

Scheme 9

Reagents: i , RONa, ROH; ii. H2S04, HgS04; i i i .RNHNH2

Scheme 10

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94 Organophosphorus Chemistry

like transition state (48) is proposed to account for this

diastereospecif ic conjugate addition. 31

reacts highly selectively at one face of the enone. depending on the

configuration of the oxide and the geometry of its double bond.

Thus the phosphine oxide

The stereochemistry of low-temperature olefination with diethyl

l-carbomethoxyethylphosphonate ( 4 9 ) depends on the structure of the

aldehyde used. 32

(El-alkenes predominate with a,@-unsaturated aldehydes. Similar

olefinations using (l-carbomethoxyethy1)diphenylphosphine oxide (50)

give predominantly (E_)-alkenes irrespective of the aldehyde

structure; thus the latter reagent can be used as a more reactive

alternative to the corresponding phosphonium ylide.

a-Branched aldehydes give mixtures and

Warren has applied his phosphine oxide-based olefination method

(involving formation and separation of the diastereomeric

2-hydroxyalkylphosphine oxide precursors of the alkene isomers) to

the stereospecific synthesis of (J3)- and (Z)-unsaturated acids

(Scheme 11). The intermediate 2-hydroxyalkylphosphine oxides (51)

are best prepared by acylation of the copper derivative of the

appropriate phosphine oxide followed by reduction. The

diastereomers of (51) were separated y& their lactones (52). A

similar method has been used to prepare the diene ( 5 4 ) en route to a

portion of the dihydrocompactin structure. 34 Reduction of the

ketone (53) to the Corresponding 2-hydroxyalkylphosphine oxide

followed by base-treatment without separation of the diastereomers

gave a (11:l) (E_:z) alkene mixture (Scheme 12).

33

a-Hydroxydienes (58), useful after modification for the

generation of trans-fused bicyclic compounds y& intramolecular

Diels-Alder reactions, have been synthesized (Scheme 13) .35

8-hydroxyalkylphosphine oxide (55) undergoes cationic rearrangement

in good to excellent yield exclusively to the y-acetate ( 5 6 ) .

usually as the (E)-isomer. The phosphine oxide-

The

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3: Phosphine Oxides and Related Compounds 95

0 I t i - iii

Ph2PCH2R1 --* I

0 II

R2PCHMeCOOMe

(49) R = OEt

( 5 0 ) R = Ph

iv 4

vi -viii and -

R’ I=\(CH~),COOH

Reagents: i, BuLi; ii, C u l l ; iii, ClCO(CH2),,C&; iv. NaBHq; v, CgCOOH;

vi, separate diastereorncrs; vii, 2 KOH, H20, THF; viii, KOH, DMSO

Scheme 11

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96 Organophosphorus Chemistry

olefination procedure with two moles of base converts the alcohol of

(56) to the product (e.g. 58); the stereochemistry of the double

bond in (56) remains unchanged. Attempts to separate the isomers at

the initial adduct stage (57). and hence control the stereochemistry

of the second double bond, were unsuccessful. The rearrangement of

(55) to (56) shows very low stereoselectivity and both diastereomers

of (55) give similiar diastereomeric mixtures of (56). 36

rearrangement of the corresponding p-nitrobenzoate esters of (55) is

highly stereospecific, e.g. - (59) giving (60). Alternatively one

diastereomer (62) can be prepared by the stereoselective reduction

of the allylic ketone (61) by lithium tri-s-butylborohydride

(L-selectride). Both allylic (63) and 6-hydroxyallylic (65)

However,

phosphine oxides have been epoxidized by m-chloroperbenzoic acid

(usually with high stereoselectivity induced by the PhzP(0) or

hydroxy groups ) to give (64) and (66). re~pectively.~~

reaction has potential in generating individual diastereomeric

Thus the

2-hydroxyalkylphosphine oxides by stereospecific epoxide

ring-opening and hence a variety of individual alkene isomers.

Diazomethylphosphoryl carbanions, have been used to prepare the

tetrazoles (67) (Scheme 141~' and 8-bromo(benzo)cyclooctatrienes

(68) .39

Reactions of tris(aminomethy1)phosphine oxide (69) with

chloroformates, isocyanates, thiocyanates, ureas, carbonyl sulphide,

and carbon disulphide give the corresponding carbamates (70). ureas

(71). and thioureas (72) . 4 0 Cyclic urea and thiourea derivatives

(73) have been obtained by thermolysis of the carbonyl sulphide and

carbon disulphide adducts.

7 Phosphine Oxide Complexes and Extractants

The q2-thiophosphinito complexes (74) undergo stepwise addition of

activated alkynes to give (75) and then (76).41

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3: Phosphine Oxides und Related Compounds 97

SiRs

( 5 4 )

Reagents: i, Bui2AIHZ; ii, NaH, THF

Scheme 12

0 iii , RZ

0

Phz!& R' R3 R 3

(55) (56)

. .. II Ph2PCHzR' I ' ' I

R'

2xi. i v ,v 1 OH

Phz R4HC& OH &

R' R4HC R' 1 OH (58)

( 57) Reagents: i, BuLi; ii, $CO&,3; iii. AczO, AcOH, TsOH; iv, R4CHO; v, NHbCI; vi, NaH, DMF

Scheme 13

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98 Organophosphorus Chemistry

OCOAr

Ph2!+ R’ R3 Ph/!+ R‘ R3

0 OCOAr

(59) (60)

(63) (64)

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3: Phosphine Oxides and Related Compounds 99

2 CF,SO, CF3SOT

l i i

0 i1

R22NHpR12 7-\ R ~ ~ N

(0 1 P R' 2

(67)

Reagents: i, Et3N; ii, Et3N, [ R22:9]0 2 CF3SOf

R22N 2

Scheme 14

0 D B r + AgCPR'R2 I I -

- .' II N 2

NPC\PR1 R 2 II

cu** (acac)

0

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100 Organophosphorus Chemistry

(70) X = COOR

(71) X = CONHR

(72) X = CSNHR (73) X = O or S

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3: Phosphine Oxides and Related Compounds 101

A variety of phosphine oxide-phosphorus ester mixtures have 4 2

been investigated in synergistic extractions of rare-earth metals,

copper, zinc, etc. 43 Halogenated hydrocarbons can be removed from

drinking water by extraction with alkylphosphine oxides on inert

supports.44

widely used extractants for metals, e.g. for niobium,45 tantalum,

Trioctylphosphine oxide continues to be one of the most 4 6

the

and

1. 2.

3.

4.

5.

6.

7.

a . 9. 10.

11. 12. 13.

14.

15.

16. 17.

18. 19. 20.

21.

22.

23. 24.

25. 26. 27. 28.

noble metals, 47 vanadium, 48 uranium, 4 9 rhenium, 50 lanthanides

actinides.51

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