Relative energetics of modes for phosphorane formation and decomposition in nucleophilic displacement reactions at acyclic phosphorus. Alkaline hydrolysis of alkoxy(alkylthio)phosphonium salts

Kenneth E. DeBruin; David M. Johnson

doi:10.1021/ja00795a034

Relative energetics of modes for phosphorane formation and decomposition in nucleophilic displacement reactions at acyclic phosphorus. Alkaline hydrolysis of alkoxy(alkylthio)phosphonium salts

Journal of the American Chemical Society ◽

10.1021/ja00795a034 ◽

1973 ◽

Vol 95 (14) ◽

pp. 4675-4681 ◽

Cited By ~ 15

Author(s):

Kenneth E. DeBruin ◽

David M. Johnson

Keyword(s):

Alkaline Hydrolysis ◽

Phosphonium Salts ◽

Nucleophilic Displacement ◽

Displacement Reactions ◽

Hydrolysis Of

ChemInform Abstract: RELATIVE ENERGETICS OF MODES FOR PHOSPHORANE FORMATION AND DECOMPOSITION IN NUCLEOPHILIC DISPLACEMENT REACTIONS AT ACYCLIC PHOSPHORUS, ALKALINE HYDROLYSIS OF ALKOXY(ALKYLTHIO)PHOSPHONIUM SALTS

Chemischer Informationsdienst ◽

10.1002/chin.197338287 ◽

1973 ◽

Vol 4 (38) ◽

pp. no-no

Author(s):

KENNETH E. DEBRUIN ◽

DAVID M. JOHNSON

Keyword(s):

Alkaline Hydrolysis ◽

Phosphonium Salts ◽

Nucleophilic Displacement ◽

Displacement Reactions ◽

Hydrolysis Of

ChemInform Abstract: THE CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS PART 6, ALKALINE HYDROLYSIS OF 1-METHYLPYRROL-2-YL- AND 1-METHYLPYRROL-2-YL-METHYL-PHOSPHONIUM SALTS, A COMPARISON WITH 2-FURYL, 2-THIENYL, PHENYL, AND RELATED HETEROARYLMETHYL AND BENZY

Chemischer Informationsdienst ◽

10.1002/chin.197509326 ◽

1975 ◽

Vol 6 (9) ◽

Author(s):

DAVID W. ALLEN ◽

BARRIE G. HUTLEY ◽

MALCOLM T. J. MELLOR

Keyword(s):

Alkaline Hydrolysis ◽

Phosphonium Salts ◽

Hydrolysis Of

Kinetics of Alkaline Hydrolysis of Quaternary Phosphonium Salts. The Influence of Protic and Aprotic Solvents on the Hydrolysis of Alkyl Phenylphosphonium Salts

Phosphorus Sulfur and Silicon and the Related Elements ◽

10.1080/10426507.2012.681409 ◽

2012 ◽

Vol 187 (10) ◽

pp. 1261-1268 ◽

Cited By ~ 8

Author(s):

J. Graham Dawber ◽

R. Glynn Skerratt ◽

John C. Tebby ◽

Albert A. C. Waite

Keyword(s):

Alkaline Hydrolysis ◽

Aprotic Solvents ◽

Phosphonium Salts ◽

Kinetics Of ◽

Hydrolysis Of ◽

Quaternary Phosphonium Salts

KINETICS OF ALKALINE HYDROLYSIS OF QUATERNARY PHOSPHONIUM SALTS. THE DEPENDENCE OF MEDIUM EFFECTS ON THE STRUCTURE OF THE SALTS

Phosphorous and Sulfur and the Related Elements ◽

10.1080/03086648408077568 ◽

1984 ◽

Vol 19 (1) ◽

pp. 99-105

Author(s):

J. Graham Dawber ◽

John C. Tebby ◽

Albert A. C. Waite

Keyword(s):

Alkaline Hydrolysis ◽

Phosphonium Salts ◽

Medium Effects ◽

Kinetics Of ◽

Hydrolysis Of ◽

Quaternary Phosphonium Salts

The alkaline hydrolysis of sterically crowded phosphonium salts

Journal of the Chemical Society C Organic ◽

10.1039/j39710001930 ◽

1971 ◽

pp. 1930 ◽

Cited By ~ 4

Author(s):

J. R. Corfield ◽

N. J. De'Ath ◽

S. Trippett

Keyword(s):

Alkaline Hydrolysis ◽

Phosphonium Salts ◽

Hydrolysis Of

ChemInform Abstract: KINETICS OF ALKALINE HYDROLYSIS OF QUATERNARY PHOSPHONIUM SALTS. THE INFLUENCE OF APROTIC SOLVENTS ON THE HYDROLYSIS OF ETHYL(PHENYL)PHOSPHONIUM IODIDES.

Chemischer Informationsdienst ◽

10.1002/chin.198411263 ◽

1984 ◽

Vol 15 (11) ◽

Author(s):

J. G. DAWBER ◽

J. C. TEBBY ◽

A. A. C. WAITE

Keyword(s):

Alkaline Hydrolysis ◽

Aprotic Solvents ◽

Phosphonium Salts ◽

Kinetics Of ◽

Hydrolysis Of ◽

Quaternary Phosphonium Salts

Mechanism of nucleophilic displacement at phosphorus in the alkaline hydrolysis of phosphinate esters

Journal of the American Chemical Society ◽

10.1021/ja00805a023 ◽

1973 ◽

Vol 95 (24) ◽

pp. 8088-8096 ◽

Cited By ~ 38

Author(s):

Robert D. Cook ◽

C. E. Diebert ◽

Wolfgang. Schwarz ◽

Patricia C. Turley ◽

Paul. Haake

Keyword(s):

Alkaline Hydrolysis ◽

Nucleophilic Displacement ◽

Hydrolysis Of

The chemistry of heteroarylphosphorus compounds. Part 11. The effects of 3-furyl and 3-thienyl substituents at phosphorus on the rate and course of alkaline hydrolysis of phosphonium salts and on the decomposition of phosphonium betaines

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19780000675 ◽

1978 ◽

pp. 675 ◽

Cited By ~ 5

Author(s):

David W. Allen ◽

Barrie G. Hutley

Keyword(s):

Alkaline Hydrolysis ◽

Phosphonium Salts ◽

Hydrolysis Of

Nucleophilic Displacement Reactions at the Thiol Ester Bond. IV. General Base Catalyzed Hydrolysis of Ethyl Trifluorothiolacetate. Kinetic Evidence for the Formation of a Tetrahedral Intermediate1

Journal of the American Chemical Society ◽

10.1021/ja01096a024 ◽

1965 ◽

Vol 87 (18) ◽

pp. 4138-4147 ◽

Cited By ~ 35

Author(s):

Leo R. Fedor ◽

Thomas C. Bruice

Keyword(s):

Ester Bond ◽

Thiol Ester ◽

General Base ◽

Nucleophilic Displacement ◽

Displacement Reactions ◽

Hydrolysis Of

Lanthanum ion catalysis of nucleophilic displacement reactions of monoesters of methyl phosphonic acid

Canadian Journal of Chemistry ◽

10.1139/v69-725 ◽

1969 ◽

Vol 47 (23) ◽

pp. 4383-4387 ◽

Cited By ~ 7

Author(s):

R. J. Withey

Keyword(s):

Aqueous Solution ◽

Phosphonic Acid ◽

Methylphosphonic Acid ◽

Nucleophilic Displacement ◽

Displacement Reactions ◽

Lanthanum Ion ◽

Rate Of Hydrolysis ◽

Catalytic Effects ◽

Hydrolysis Of

The catalytic effects of lanthanum ion on the rate of hydrolysis of p-nitrophenyl hydrogen methylphosphonate in aqueous solution at pH > 7.0 are reported. Increases in rate by a factor of about 3.6 × 104 have been observed. No such catalysis was found for diesters of methylphosphonic acid.