Organometallic Syntheses

Nontransition-Metal Compounds

1st Edition - August 28, 1981
Editor: John Eisch
Language: English
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 1 6 0 1 7 - 9

Nontransition-Metal Compounds is the second volume in the series Organometallic Syntheses and presents various procedures for the nontransition-metal compounds. Topics also covered… Read more

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Nontransition-Metal Compounds is the second volume in the series Organometallic Syntheses and presents various procedures for the nontransition-metal compounds. Topics also covered in this volume include sensitive liquids, sample transfer, and inert atmosphere provision. The text is divided into two major parts. Part I is mostly procedural as it offers directions and suggestions in different processes such as (a) establishment of an inert atmosphere and solvent medium; (b) evaluation of purity, mode of mixing, and solvent type; and (c) isolation and purification of reaction products. Organometallic products, particularly its physical and chemical characteristics, are also tackled. In Part II, around 85 nontransition-metal organometallic compounds and the reliable procedures used for their synthesis are presented. This particular volume will be of help to students both in the fields of chemistry and biology.

Foreword

Preface

Part I General Experimental Techniques in the Organometallic Chemistry of Nontransition Metals

A. Establishment of Anhydrous and Anaerobic Reaction Media

1. General Reactivity Considerations for σ-Bonded Organometallics

2. Inert Gases

3. Inert Solvents

4. Drying and Deoxygenating the Reaction Zone

5. Storage and Transfer of Organometallic Compounds

B. Execution of Organometallic Reactions

1. Purity of Reagents

2. State of Subdivision

3. Solvent

4. Mode of Admixing

5. Temperature Control

6. Catalysts and Promoters

7. Precipitation and Filtration

8. Gas Evolution

9. Monitoring the Course of Reaction

C. Purification of Organometallic Products

1. Consideration of Thermal and Light Instability

2. Complex Formation

3. Extraction

4. Chromatography

5. Recrystallization

6. Distillation

D. Characterization of Organometallic Compounds

1. Physical Properties

2. Elemental Analysis

3. Molecular Weight

4. Hydrolysis and Other Carbon-Metal Bond Cleavages

5. Spectroscopy

?. Safety Measures

1. General Precautions

2. Toxicity Dangers

3. Fire Hazards

4. Explosions

Part II Specific Preparations of Nontransition-Metal Organometallic Compounds

A. Introduction

1. Criteria Governing the Choice of Procedures

2. General Procedural Observations

B. Compounds of Group IA

1. General Preparative and Analytical Methods

2. Allyllithium

3. p-Bromophenyllithium

4. Benzyllithium

5. Phenoxymethyllithium

6. Diphenylmethyllithium

7. Triphenylmethyllithium

8. (E,E)-1,2,3,4-Tetraphenyl-1,3-butadien-1,4-ylidenedilithium

C. Compounds of Group IIA

1. General Preparative and Analytical Methods

2. α-Deuteriovinylmagnesium Chloride

3. Allylmagnesium Bromide

4. Diallylmagnesium

5. 3-(1-Bromomagnesiooxy-1-cyclohexyl)-propylmagnesium Bromide

6. (E)-2-Phenyl-1-phenylsulfonylvinyllithium and (E)-2-Phenyl-1-phenylsulfonylvinylmagnesium Bromide

D. Compounds of Group IIB

1. General Preparative and Analytical Methods

2. Ethylzinc Halide

3. Diethylzinc

4. Di-1-alkynylmercury

5. Bis(trimethylsily)mercury

6. Phenylmercuric Bromide

7. Diphenylmercury

8. Bis[(E)-stilbenyl]mercury and Bis[(Z)-stilbenyl]mercury

E. Compounds of Group IIIA

1. General Preparative and Analytical Methods

2. 1-Methyl-4,5-dihydroborepin and 1-Chloro-4,5-dihydroborepin

3. Phenylborane-Triethylamine

4. Phenylboron Dibromide and Diphenylboron Bromide

5. 1-Phenylboracyclopentane

6. Triphenylborane

7. Diphenyl(phenylethynyl)borane-Pyridine

8. Pentaphenylborole

9. Heptaphenyl-7-borabicyclo[2.2.1]heptadiene

10. Heptaphenylborepin

11. Salts of the Bis(2,2'-biphenylene)borate Anion

12. Diisobutylaluminum Deuteride

13. Diisobutyl[(Z)-1-trimethylsilyl-2-phenylethenyl]aluminum

14. Diphenylaluminum Chloride and Phenylaluminum Dichloride

15. Triphenylaluminum

16. Diphenyl(phenylethynyl)aluminum

17. Tribenzylaluminum

18. Diethylgallium Chloride

19. Diethylgallium Ethoxide

20. Triethylgallium

21. Triisobutylgallium

22. Triphenylgallium

23. Tri-n-decylgallium

24. Diethylindium Chloride

25. Triethylindium

26. Triisobutylindium

27. Triphenylindium

28. Thallium(I) Cyclopentadienide

29. Diphenylthallium Halide

30. Triphenylthallium

F. Compounds of Group IVA

1. General Preparative and Analytical Methods

2. 1,1-Dimethyl-2,5-dihydrobenzo[c]silole

3. Trimethyl(phenylethynyl)silane

4. Trimethyl(cis-β-styryl)silane and Trimethyl(trans-?-styryl)silane

5. Triphenylsilylpotassium and Triphenylsilyllithium

6. Hexaphenyldisilane

7. 1,4-Bis(triphenylsilyl)butane

8. Bromo(triphenyl)germane and Chloro(triphenyl)germane

9. Triphenyl(vinyl)germane

10. Tetraphenylgermane

11. Hexamethylditin

12. Di-n-butyltin Dihydride

13. Trimethyl(phenylethynyl)tin

14. Tri-n-butyl(iodomethyl)tin

15. 1,1-Di-n-butyl-4,5-dihydrostannepin

16. Chloro(triphenyl)tin and Dichloro(diphenyl)tin

17. Triphenyltin Hydride

18. Tri-n-butyl(phenoxymethyl)tin

19. Allyl(triphenyl)tin and Diallyl(diphenyl)tin

20. Triphenyl(trans-β-styryl)tin

21. 1,1-Dimethyl-2,3,4,5-tetraphenylstannole

22. Halo(triphenyl)lead and Dihalo(diphenyl)lead

23. Allyl(triphenyl)lead

24. Tetraphenyllead

Appendix I. Bibliography of Compilations on Organometallic Chemistry

Appendix II. Suppliers of Reagents for Organometallic Chemistry

Appendix III. Special Solvents for Organometallic Reagents

Appendix IV. Periodic Table of the Main-Group Elements

Index of Compounds