Phosphinite

Short description: Organic compounds of the formula P(OR)R2

Not to be confused with phosphonite (formula P(OR)2R) .

Structural formula of a generic phosphinite, R represents a side chain. Skeletal formula of methyl diphenylphosphinite

In organic chemistry, phosphinites are organophosphorus compounds with the formula P(OR)R
2. They are used as ligands in homogeneous catalysis and coordination chemistry.[1]

## Contents

* 1 Preparation
* 2 Reactions
* 3 References
* 4 See also

## Preparation

Phosphinites are prepared by alcoholysis of organophosphinous chlorides. For example, treatment of chlorodiphenylphosphine with methanol and base gives methyl diphenylphosphinite:

ClPPh2 \+ CH3OH → CH3OPPh2 \+ HCl

Although they are esters of phosphinous acids (R2POH), phosphinites are not made via such intermediates.

## Reactions

Oxidation of phosphinites gives phosphinates:

2 P(OR)R2 \+ O2 → 2 OP(OR)R2

Phosphinites are ligands, giving derivatives similar to metal phosphine complexes. They are stronger pi-acceptors than typical phosphine ligands.[2]

## References

1. ↑ D. E. C. Corbridge (1995). Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology (5th ed.). Amsterdam: Elsevier. ISBN 0-444-89307-5.
2. ↑ Rajanbabu, T. V. Babu (2012). "Phosphinite and Phosphonite Ligands". Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis. pp. 159–232. doi:10.1002/9781118299715.ch5. ISBN 9781118299715.

## See also

* Phosphine \- PR3
* Phosphine oxide \- OPR3
* Phosphonite \- P(OR)2R
* Phosphite - P(OR)3
* Phosphinate \- OP(OR)R2
* Phosphonate \- OP(OR)2R
* Phosphate \- OP(OR)3

* v
* t
* e

Organophosphorus

Only P-O bonds|

| P(III)|

* Phosphite/Organophosphite

|

P(V)|

* Phosphate/Organophosphate

With P-C bonds|

| One P-C bonds|

| P(III)|

* Phosphonite

|

P(V)|

* Phosphonate

Two P-C bonds|

| P(III)|

* Phosphinite

|

P(V)|

* Phosphinate

Three P-C bonds|

| P(III)|

* Phosphine

|

P(V)|

* Phosphine oxide

With P-N bonds|

| One P-N bond|

| P(III)|

* Phosphoramidite
* e.g. Nucleoside phosphoramidite

|

P(V)|

* Phosphoramidate
* e.g. Phosphocreatine

Two P-N bond|

| P(III)|

* Phosphorodiamidite

|

P(V)|

* Phosphorodiamidate
* e.g. Morpholino
* Cyclophosphamide

Three P-N bond|

| P(V)|

* Phosphoramide
* e.g. Hexamethylphosphoramide
* Metepa

|

With P-C and P-N bonds|

| One P-C bond and one P-N bond|

| P(V)|

* Phosphonamidate

|

One P-C bond and two P-N bond|

| P(V)|

* Phosphonamide

|

Two P-C bond and one P-N bond|

| P(V)|

* Phosphinamide

|

With P-S bonds|

| One P-S bond|

| P(III)|

* Phosphorothioite

|

P(V)|

* Phosphorothioate

Two P-S bond|

| P(III)|

* Phosphorodithioite

|

P(V)|

* Phosphorodithioate

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