Best Synthetic Methods - 1st Edition - ISBN: 9780080982120, 9780080982243

Best Synthetic Methods

1st Edition

Organophosphorus (V) Chemistry

Authors: Chris Timperley
eBook ISBN: 9780080982243
Hardcover ISBN: 9780080982120
Imprint: Academic Press
Published Date: 4th December 2014
Page Count: 786
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Description

Best Synthetic Methods: Organophosphorus (V) Chemistry provides systematic coverage of the most common classes of pentavalent organophosphorus compounds and reagents (including phosphonyl, phosphoryl, and organophosphates), and allows researchers an easy point of entry into this complex and economically important field. The book follows the Best Synthetic Methods format, containing practical methods, synthetic tips, and shortcuts. Where relevant, articles include toxicity data and historical context for the reactions. Typical analytical and spectroscopic data are also presented to enable scientists to identify key compound characteristics.

The book is a valuable companion to research chemists in both academia and industry, summarizing the best practical methods (often originating in difficult-to-access, foreign-language primary literature) in one place. It is ideally suited for those working on industrial applications of these compounds, including insecticides, herbicides, flame retardants, and plasticizers.

Key Features

  • Includes a mixture of tried and tested, historical methods that are proven to work, alongside new methods to provide scientists with a quick, time-saving resource of reliable methods
  • Includes tips and tricks to get reactions to work; important information often missing from other sources
  • Includes key analytical data for compounds, so scientists have one handy resource to select, perform, and analyze the best reaction

Readership

Post graduates, postdocs and researchers in chemistry, engineering and materials science

Table of Contents

  • Preface
  • Chapter 1. General Overview
    • 1.1. Introduction
    • 1.2. Natural Occurrence of Phosphorus
    • 1.3. Principal Compounds of Phosphorus
    • 1.4. Phosphorus Compounds in Living Systems
    • 1.5. A Brief History of Synthetic Organophosphorus Chemistry
    • 1.6. Nomenclature of Organophosphorus Compounds
    • 1.7. Chiral Phosphorus Compounds and Biological Implications
    • 1.8. Phosphorus-Containing Pharmaceuticals
    • 1.9. Fire Retardants and Fire-Extinguishing Compounds
    • 1.10. Toxicology and Medical Treatment of organophosphorus Compounds
    • 1.11. Fluorogenic Nerve Agent Mimics for Screening for Improved Bioscavengers
    • 1.12. Biotinylated Nerve Agent Mimics for Activity-Based Enzyme Profiling
    • 1.13. Working Safely with Organophosphorus Compounds
  • Chapter 2. Phosphonyl Compounds
    • 2.1. Introduction
    • 2.2. Alkyl Alkyl-H-Phosphinates R(R′O)P(O)H
    • 2.3. Alkylphosphonic Dichlorides RP(O)Cl2
    • 2.4. Alkylphosphonic Dibromides RP(O)Br2
    • 2.5. Alkylphosphonic Difluorides RP(O)F2
    • 2.6. Alkylphosphonofluoridic Acids RP(O)(OH)F
    • 2.7. Alkylphosphonic Chlorofluorides RP(O)CIF
    • 2.8. Alkylphosphonic Isocyanatofluorides RP(O)(NCO)F
    • 2.9. Alkylphosphonic Isothiocyanatofluorides RP(O)(NCS)F
    • 2.10. Alkylphosphonic Diisocyanates RP(O)(NCO)2
    • 2.11. Alkylphosphonic Diisothiocyanates RP(O)(NCS)2
    • 2.12. Alkylphosphonic Acids RP(O)(OH)2
    • 2.13. Dialkyl Alkylphosphonates RP(O)(OR)2
    • 2.14. Dialkyl Arylphosphonates ArP(O)(OR)2
    • 2.15. Dialkyl α-Ketophosphonates (RO)2P(O)C(O)R′
    • 2.16. Dialkyl α-Hydroxyphosphonates (RO)2P(O)CH(OH)R′ (Pudovik Reaction)
    • 2.17. Dialkyl α-Siloxyphosphonates (RO)2P(O)CH(OSiMe3)R′ (Abramov Reaction)
    • 2.18. Dialkyl α-Aminophosphonates (RO)2P(O)CR2NR2 (Kabachnik–Fields Reaction)
    • 2.19. Dialkyl Alkenylphosphonates (RO)2P(O)C=CR2
    • 2.20. Dialkyl Alkynylphosphonates (RO)2P(O)C2P(O)C≡CR
    • 2.21. Alkyl Alkylphosphonochloridates R(R′O)P(O)Cl
    • 2.22. N,N-Dialkyl Alkylphosphonamidochloridates R(R′2N)P(O)Cl
    • 2.23. S-Alkyl Alkylphosphonochloridothiolates R(R′S)P(O)Cl
    • 2.24. Alkyl Alkylphosphonofluoridates R(R′O)P(O)F
    • 2.25. N-Alkyl or N,N-Dialkyl Alkylphosphonamidofluoridates R(R′XN)P(O)F (X = H or R′)
    • 2.26. S-Alkyl Alkylphosphonofluoridothiolates R(R′S)P(O)F
    • 2.27. Alkyl Alkylphosphonocyanidates R(R′O)P(O)CN
    • 2.28. Alkyl Alkylphosphonic Acids R(R′O)P(O)OH
    • 2.29. Alkylphosphonofluoridic Anhydrides R(F)P(O)OP(O)(F)R
    • 2.30. Dialkyl Dialkylpyrophosphonates R(R′O)P(O)OP(O)(OR′)R
    • 2.31. N,N-Dialkyl-P-Alkylphosphonamidic Anhydrides R(R′2N)P(O)OP(O)(NR′2)R
    • 2.32. S,S′-Dialkyl Dialkyldithiopyrophosphonates R(R′S)P(O)OP(O)(SR′)R
    • 2.33. O-Alkyl N-Alkyl Alkylphosphonamidates RP(O)(NR2)OR
    • 2.34. Bis(N,N-Dialkyl) Alkylphosphonodiamidates RP(O)(NR2)2
    • 2.35. O,S-Dialkyl Alkylphosphonothiolates RP(O)(OR)SR
    • 2.36. S-Alkyl N-Alkyl (or N,N-Dialkyl) Alkylphosphonamidothiolates RP(O)(NR2)SR
    • 2.37. S,S′-Dialkyl Alkylphosphonodithiolates RP(O)(SR2)2
  • Chapter 3. Thiophosphonyl Compounds
    • 3.1. Introduction
    • 3.2. Alkylphosphonothioic Dichlorides RP(S)Cl2
    • 3.3. Alkylphosphonothioic Difluorides RP(S)F2
    • 3.4. Dialkyl Alkylphosphonothionates (RO)2P(S)R
    • 3.5. Alkyl Alkylphosphonochloridothionates RO(R′)P(S)Cl
    • 3.6. Alkyl Alkylphosphonofluoridothionates RO(R′)P(S)F
    • 3.7. O-Alkyl Hydrogen Alkylphosphonothioates RO(R′)P(S)OH
    • 3.8. Dialkyl Dialkylpyrophosphonodithionates RO(R′)P(S)OP(S)(R′)OR
    • 3.9. S-Alkyl Alkylphosphonochloridothiolothionates RS(R′)P(S)Cl
    • 3.10. N,N-Dialkyl P-alkylphosphonamidochloridothionates R2N(R′)P(S)Cl
    • 3.11. N,N-Dialkyl P-alkylphosphonamidofluoridothionates R2N(R′)P(S)F
    • 3.12. Alkyl Alkylphosphonocyanidothionates RO(R′)P(S)CN
    • 3.13. Alkyl Alkyl/aryl Alkylphosphonothionates RO(R′)P(S)OR′′
    • 3.14. O-Alkyl N-alkyl/aryl Alkylphosphonamidothionates RO(R′)P(S)NR2
    • 3.15. O-Alkyl S-alkyl Alkylphosphonodithioates RO(R′)P(S)SR
    • 3.16. Bis(O-alkyl Alkylphosphinothioyl) Disulfides RO(R′)P(S)SSP(S)(R′)OR
    • 3.17. Bis(N,N-dialkyl) Alkylphosphonodiamidothionates (R2N)2P(S)R′
    • 3.18. S,S′-Dialkyl Alkylphosphonodithiolothionates (RS)2P(S)R′
  • Chapter 4. Phosphoryl Compounds
    • 4.1. Introduction
    • 4.2. Alkyl Phosphorodichloridates ROP(O)Cl2
    • 4.3. Aryl Phosphorodichloridates ArOP(O)Cl2
    • 4.4. Alkyl Phosphorodifluoridates ROP(O)F2
    • 4.5. Aryl Phosphorodifluoridates ArOP(O)F2
    • 4.6. Alkyl N,N,N′,N′-tetraalkyl Phosphorodiamidates ROP(O)(NR2)2
    • 4.7. Alkyl Phosphorodihydrazidates ROP(O)(NHNHR)2
    • 4.8. Alkyl Phosphorodiisocyanatidates ROP(O)(NCO)2
    • 4.9. Alkyl Phosphorodiisothiocyanatidates ROP(O)(NCS)2
    • 4.10. Alkyl Dihydrogen Phosphates ROP(O)(OH)2
    • 4.11. O,S,S′-Trialkyl Phosphorodithiolates ROP(O)(SR)2
    • 4.12. O,S-Dialkyl Phosphorochloridothiolates RO(RS)P(O)Cl
    • 4.13. O-Alkyl N,N-dialkylphosphoramidochloridates RO(R2N)P(O)Cl
    • 4.14. S-Alkyl N,N-dialkylphosphoramidochloridothiolates RS(R2N)P(O)Cl
    • 4.15. S,S′-Dialkyl Phosphorochloridodithiolates (RS)2P(O)Cl
    • 4.16. O,S-Dialkyl Phosphorofluoridothiolates RO(RS)P(O)F
    • 4.17. O-Alkyl N,N-dialkylphosphoramidofluoridates RO(R2N)P(O)F
    • 4.18. Symmetrical Dialkyl H-phosphonates (RO)2P(O)H
    • 4.19. Unsymmetrical Dialkyl H-phosphonates RO(R′O)P(O)H
    • 4.20. Diaryl H-phosphonates (ArO)2P(O)H
    • 4.21. Dialkyl Phosphorofluoridates (RO)2P(O)F
    • 4.22. Dialkyl Phosphorochloridates (RO)2P(O)Cl
    • 4.23. Diaryl Phosphorochloridates (ArO)2P(O)Cl
    • 4.24. Dialkyl Phosphorobromidates (RO)2P(O)Br
    • 4.25. Dialkyl Phosphoroiodidates (RO)2P(O)I
    • 4.26. Dialkyl Phosphorocyanidates (RO)2P(O)CN
    • 4.27. O-ALKYL Dialkoxyphosphinylformates (RO)2P(O)C(O)OR
    • 4.28. S-Alkyl Dialkoxyphosphinylthioformates (RO)2P(O)C(O)SR
    • 4.29. N-Alkyl Dialkoxyphosphinylformamides (RO)2P(O)C(O)NR2
    • 4.30. [(Dialkoxyphosphinyl)formyl]-O-alkylhydroxamates (RO)2P(O)C(O)NHOR
    • 4.31. S-Alkyl Dialkoxyphosphinyldithioformates (RO)2P(O)C(S)SR
    • 4.32. Symmetrical Dialkyl Hydrogen Phosphates (RO)2P(O)OH
    • 4.33. Unsymmetrical Dialkyl Hydrogen Phosphates RO(R′O)P(O)OH
    • 4.34. Dialkyl Alkylperoxy Phosphates (RO)2P(O)OOR
    • 4.35. Trialkyl Phosphates (RO)2P(O)OR
    • 4.36. Diaryl Alkyl Phosphates (ArO)2P(O)OR
    • 4.37. Triaryl Phosphates (ArO)3P=O
    • 4.38. Dialkyl Alkylideneamino Phosphates (RO)2P(O)ON=CR2 (Allen Reaction)
    • 4.39. Dialkyl Enolphosphates (RO)2P(O)OCR=CR2 (Perkow Reaction)
    • 4.40. Dialkyl Phosphorazidates (RO)2P(O)N3
    • 4.41. Dialkyl Phosphoramidates (RO)2P(O)NR2 (Todd–Atherton Reaction)
    • 4.42. Dialkyl N-arylphosphoramidates (RO)2P(O)NHAr
    • 4.43. Diaryl Phosphoramidates (ArO)2P(O)NR2
    • 4.44. Dialkyl N-methyl-N-(phosphoryl)phosphoramidates (RO)2P(O)N(Me)P(X)R2
    • 4.45. Dialkyl N-methyl-N-acylphosphoramidates (RO)2P(O)N(Me)COR′
    • 4.46. Disubstituted N-aryl(or alkyl)-N-chlorophosphoramidates (RO)2P(O)N(Cl)Ar
    • 4.47. Dialkyl N,N-dihalophosphoramidates (RO)2P(O)NX2 (X = Cl or Br)
    • 4.48. Dialkyl N-hydroxy/alkoxyphosphoramidates (RO)2P(O)NHOR (R = H or Alkyl)
    • 4.49. Dialkyl Phosphorohydrazidates (RO)2P(O)NH2NH2
    • 4.50. Dialkyl Phosphoroisocyanatidates (RO)2P(O)NCO
    • 4.51. Dialkyl Phosphoroisothiocyanatidates (RO)2P(O)NCS
    • 4.52. Dialkyl Phosphoro(thionylamidates) (RO)2P(O)NSO
    • 4.53. N,N′-Bis(dialkylphosphoryl)sulfamides (RO)2P(O)NHSO2NHP(O)(OR)2
    • 4.54. N-(Dialkylphosphoryl)aldimines (RO)2P(O)N=CHR
    • 4.55. N-(Dialkylphosphoryl)guanidines (RO)2P(O)N=C(NR2)2
    • 4.56. O,O-Dialkyl Hydrogen phosphorothioates (RO)2P(O)SH
    • 4.57. O,O,S-Trialkyl Phosphorothiolates (RO)2P(O)SR
    • 4.58. Dialkyl S-(S-alkyl) Phosphorothiolates (RO)2P(O)SSR
    • 4.59. Dialkyl S-(O-alkyl) Phosphorothiolates (RO)2P(O)SOR
    • 4.60. Dialkylphosphoryl Alkylsulfonates (RO)2P(O)S(O)OR
    • 4.61. Tetraalkyl Pyrophosphates (RO)2P(O)OP(O)(OR)2
    • 4.62. Bis(dialkylphosphoryl) Sulfides (RO)2P(O)SP(O)(OR)2
    • 4.63. Bis(dialkylphosphoryl) Disulfides (RO)2P(O)SSP(O)(OR)2
    • 4.64. Bis(dialkylphosphoryl) Sulfoxides (RO)2P(O)S(O)P(O)(OR)2
    • 4.65. N-Alkylphosphoramidic Dichlorides RNHP(O)Cl2
    • 4.66. N,N-Dialkylphosphoramidic Dichlorides R2NP(O)Cl2
    • 4.67. N,N-Dialkylphosphoramidic Difluorides R2NP(O)F2
    • 4.68. N,N,N′,N′-Tetraalkyl Phosphorodiamidites (R2N)2P(O)H
    • 4.69. N,N,N′,N′-Tetraalkyl Phosphorodiamidochloridates (R2N)2P(O)Cl
    • 4.70. Bis(N-alkyl) or N,N,N′,N′-tetraalkyl Phosphorodiamidofluoridates (R2N)2P(O)F
    • 4.71. N,N,N′,N′-Tetraalkyl Phosphorodiamidoazidates (R2N)2P(O)N3
    • 4.72. Bis(N,N-dialkyl) Pyrophosphorodiamidates (R2N)2P(O)OP(O)(NR2)2
    • 4.73. Tri- and hexaalkylphosphoramides (RNH)3P=O and (R2N)3P=O
  • Chapter 5. Thiophosphoryl Compounds
    • 5.1. Introduction
    • 5.2. Alkyl Phosphorodichloridothionates ROP(S)Cl2
    • 5.3. Dialkyl H-thiophosphonates (RO)2P(S)H
    • 5.4. Dialkyl Phosphorochloridothionates (RO)2P(S)Cl
    • 5.5. Dialkyl Phosphorocyanidothionates (RO)2P(S)CN
    • 5.6. O,O-Dialkyl Hydrogen Phosphorothioates (RO)2P(S)OH
    • 5.7. Trialkyl (or Dialkyl Aryl) Phosphorothionates (RO)2P(S)OR′
    • 5.8. Dialkyl Enol Phosphorothionates (RO)2P(S)OCR=CR2′
    • 5.9. O,O-Dialkyl O-oximino Phosphorothionates (RO)2P(S)ON=CR2′
    • 5.10. O,O-Dialkyl O-acyl Phosphorothionates (RO)2P(S)OC(O)R′
    • 5.11. Dialkyl Phosphoramidothionates (RO)2P(S)NH2
    • 5.12. S,S-Dialkyl Phosphoramidodithiolothionates (RS)2P(S)NHR′
    • 5.13. Tris(N,N-dialkylamino)Phosphorothionates (R2N)3P=S
    • 5.14. Disubstituted N-(alkoxy)Phosphoramidothionates (RO)2P(S)NHOR′
    • 5.15. Dialkyl Phosphorohydrazidothionates (RO)2P(S)NR′NR2′
    • 5.16. Dialkyl PhosphoroisoCYANATIDOthionates (RO)2P(S)NCO
    • 5.17. Dialkyl Phosphoroisothiocyanatidothionates (RO)2P(S)NCS
    • 5.18. Dialkyl Phosphorazidothionates (RO)2P(S)N3
    • 5.19. Dialkyl N-(phosphinimido)Phosphorothionates (RO)2P(S)N=PR3′
    • 5.20. O,O-Dialkyl S-(dialkylamino) Phosphorothiolothionates (RO)2P(S)SNR2′
    • 5.21. O,O-Dialkyl Hydrogen Phosphorodithioates (RO)2P(S)SH
    • 5.22. O,O-Dialkyl S-alkyl Phosphorothiolothionates (RO)2P(S)SR′
    • 5.23. O,O-Dialkyl S-(alkyl/aryl-thio) Phosphorodithioates (RO)2P(S)SSR′
    • 5.24. O,O-Dialkyl S-(dialkylaminothio) Phosphorodithioates (RO)2p(S)SSNR2′
    • 5.25. O,O-Dialkyl S-(alkoxy) Phosphorodithioates (RO)2P(S)SOR′
    • 5.26. O,O-Dialkyl S-acyl Phosphorodithioates (RO)2P(S)SC(O)R′
    • 5.27. O,O-Dialkyl S-(N-alkylcarbamoyl) Phosphorodithioates (RO)2P(S)SC(O)NR2′
    • 5.28. Tetra-Alkyl Pyrophosphorodithionates (RO)2P(S)OP(S)(OR)2
    • 5.29. Tetra-Alkyl Pyrophosphorothionates (RO)2P(S)OP(O)(OR)2
    • 5.30. Tetra-Alkyl Thiopyrophosphorodithionates (RO)2P(S)S(S)P(OR)2
    • 5.31. Bis(Dialkylthiophosphoryl) Disulfides (RO)2P(S)SSP(S)(OR)2
    • 5.32. Tetra-Alkyl Carbonyl bis(phosphorodithioates) [(RO)2P(S)S]2C=O
  • Chapter 6. Selenophosphorus Compounds
    • 6.1. Introduction
    • 6.2. Alkali Metal O,O-dialkyl Phosphoroselenoates (RO)2P(O)SeM
    • 6.3. Dialkyl Phosphorochloridoselenonates (RO)2P(Se)Cl
    • 6.4. Dialkyl Hydrogen Phosphoroselenoates (RO)2P(Se)OH and Phosphono and Phosphino Relatives: RO(R)P(Se)OH and R2P(Se)OH
    • 6.5. Nucleoside H-phosphonoselenoate Monoesters (RO)P(O)(H)SeH and Diesters (RO)2P(Se)H
    • 6.6. O,O,Se-Trisubstituted Phosphoroselenolates (RO)2P(O)SeR′
    • 6.7. Tetra-Alkyl Selenopyrophosphates (RO)2P(O)SeP(O)(OR)2 and bis(Dialkylphosphoryl) Diselenides (RO)2P(O)SeSeP(O)(OR)2
    • 6.8. O,O-Dialkyl Phosphoroselenothioate Salts (RO)2P(S)SeM or (RO)2P(Se)SM and O,O,Se-trialkyl Phosphoroselenothionates (RO)2P(S)SeR or O,O,S-trialkyl Phosphoroselenothiolates (RO)2P(Se)SR
    • 6.9. O,O,O-Trisubstituted Phosphoroselenonates (RO)3P=Se
    • 6.10. O,O-Dialkyl Phosphorodiselenoate Salts (RO)2P(Se)SeM and O,O,Se-trialkyl Phosphorodiselenoates (RO)2P(Se)SeR′
    • 6.11. Halogenoselenophosphonium Salts [R3P+SeX]X− and [(RO)3P+SeX]X−
    • 6.12. Secondary Phosphine Selenides R2P(Se)H
    • 6.13. Tertiary Phosphine Selenides R3P=Se
    • 6.14. Disubstituted Phosphinochloridoselenonates R2P(Se)Cl
    • 6.15. Diselenophosphinoic Acid Salts R2P(Se)SeM
    • 6.16. Esters of Diselenophosphinoic Acids R2P(Se)SeR′
    • 6.17. Bis(dialkylselenophosphinyl) Selenides [R2P(Se)]2Se and Diselenides [R2P(Se)]2Se2
    • 6.18. Dialkyl Phosphinoselenothioate Salts R2P(S)SeM and Se-esters R2P(S)SeR′
    • 6.19. Woollin's REAGENT (WR) and Phosphorus–Selenium-Containing Derivatives
  • Chapter 7. Analysis of Organophosphorus Chemicals
    • 7.1. Introduction
    • 7.2. Some Important Organophosphorus Chemicals
    • 7.3. Analytical Techniques for the Analysis of Organophosphorus Chemicals
    • 7.4. Concluding Comments
  • Index

Details

No. of pages:
786
Language:
English
Copyright:
© Academic Press 2014
Published:
Imprint:
Academic Press
eBook ISBN:
9780080982243
Hardcover ISBN:
9780080982120

About the Author

Chris Timperley

Affiliations and Expertise

Defence Science and Technology Laboratory (Dstl), Porton Down, Wiltshire, UK