ORGANOMETALLIC COMPOUNDS

Transcription

1 ORGANOMETALLIC COMPOUNDS METHODS OF SYNTHESIS PHYSICAL CONSTANTS AND CHEMICAL REACTIONS Edited by MICHAEL DUB Central Research Department, Monsanto Company Volume II COMPOUNDS OF GERMANIUM, TIN AND LEAD INCLUDING BIOLOGICAL ACTIVITY AND COMMERCIAL APPLICATION Second Edition, Edited by RICHARD W. WEISS Organic Division, Monsanto Company Covering the Literature from 1937 to 1964 SPRINGER-VERLAG BERLIN HEIDELBERG NEW YORK 1967

2 CONTENTS PREFACE TO THE SECOND EDITION INTRODUCTION TO VOLUME II ABBREVIATIONS III V VII GERMANIUM 1. Symmetrie Tetraorganogermanes 1 2. Unsymmetric Tetraorganogermanes 2.1 Nonfunctional Derivatives Unsymmetric Tetraorganogermanes with Oleflnic Substituents Unsymmetric Tetraorganogermanes Containing Functionally Substituted Olefinic Groups Unsymmetric Tetraorganogermanes with Acetylenic Substituents Unsymmetric Tetraorganogermanes Containing Functionally Substituted Acetylenes Functionally Substituted Unsymmetric Tetraorganogermanes Tetraorganogermanes Containing Halogen Tetraorganogermanes Containing Pseudohalogen Substituents Tetraorganogermanes Containing Oxygen Organogermanes with Hydroxy Groups and Their Derivatives «3 Tetraorganogermanes Containing Carbonyl Groups Tetraorganogermanes Containing Carboxyl Functions Tetraorganogermanes Containing Sulfur Tetraorganogermanes Containing Nitrogen and Phosphorous Tetraorganogermanes Containing Metal Substituents Bridged Bisorganogermanes Tetraorganogermanes Containing Organosilyl Substituents Tetraorganogermanes Containing Organotin Substituents Tetraorganogermanes Containing Group II Metals Tetraorganogermanes Containing Alkali Metals Organogermanium Hydrides 3.1 Nonfunctional Organogermanium Hydrides Unsymmetric Organogermanium Hydrides Deuterium-Substituted Organogermanium Hydrides Functionally Substituted Organogermanium Hydrides Organogermanium Hydrides Containing Heteroatom- Germanium Bonds 63 3,8.1 Mixed Organogermanium Hydride Halides 63 3,8.3 Organogermanium Hydrides Containing Other Germanium- Heteroatom Bonds 65 XI

3 4. Organogermanium Compounds Containing Heteroatom- Germanium Bonds 4.1 Compounds with Halogen Triorganogermanium Halides Unsubstituted Symmetrie Triorganogermanium Halides Unsymmetric Unsubstituted Triorganogermanium Halides Functionally Substituted Triorganogermanium Halides Diorganogermanium Dihalides Unsubstituted Diorganogermanium Dihalides Functionally Substituted Diorganogermanium Dihalides Organogermanium Trihalides Unsubstituted Organogermanium Trihalides Uhsaturated Organogermanium Trihalides Functionally Substituted Organogermanium Trihalides Organogermanium Salts Organogermanium Pseudohalides Organogermanium Salts or Esters of Oxygen Acids Organogermanes with Germanium Oxygen-Bonds Organogermanium Oxides and Hydroxides Triorganogermanium Oxides and Hydroxides Diorganogermanium Oxides Monoorganogermanium Oxides and Germanoic Acids Organogermanium Peroxy Compounds Organogermanium Alkoxides and Mixed Oxides Organogermanium Carboxylates Organogermanium Carboxylates with Unsubstituted Carboxylic Acids Organogermanium Carboxylates Derived from Functionally Substituted Carboxylic Acids Organogermanium Compounds with Sulfur and Selenium Organogermanium Sulfides, Disulfides, and Selenides Organogermanium Mercaptides and Mercaptans Metal-Substituted Organogermanium Sulfides and Selenides Organogermanium Compounds with Nitrogen, Phosphorous, Arsenic, Antimony, and Bismuth Organogermanium Amides, Imides, Nitrides, and Phosphides Organogermanium Metal Imides Organogermanium Imido Phosphoranes and Arsenic or Antimony Analogues Organo-polygermanes Hexaorganodigermanes Organo-polygermanes Containing More Than Two Germanium Atoms Organo-polygermanes Containing Heteroatoms Bimetallic Organogermanes 6.1 Organogermanes Containing Germanium-Metal Bonds Bimetallic Organogermanium Derivatives with Metal Coordination Compounds 138 XII

4 7. Cyclic Organogermanes 7.1 Cyclic Tetraorganogermanes Cyclic Organogermanium Hydrides Cyclic Organogermanium Compounds Containing Heteroatom- Germanium Bonds Cyclic Organogermanium Halides Cyclic Organogermanes with Germanium-Oxygen Bonds Cyclic Organo-polygermanes Polymerization Reactions with Organogermanes. 155 TIN 1. Symmetrie Tetraorganotin Compounds 1.1 Nonfunctional Symmetrie Tetraorganotin Compounds Symmetrie Tetraheterocyclic Tin Compounds Symmetrie Unsaturated Tetraorganotin Compounds Symmetrie Functionally Substituted Tetraorganotin Compounds Symmetrie Halogen-Substituted Tetraorganotin Compounds Other Symmetrie Functionally Substituted Tetraorganotin Compounds Unsymmetric Tetraorganotin Compounds Unsymmetric Nonfunctional Tetraorganotin Compounds Heterocyclic Substituted Tetraorganotin Compounds Tetraorganotin Compounds with Olefinic Substituents Tetraorganotin Derivatives of Functionally Substituted Olefins Tetraorganotin Compounds with Acetylenic Substituents Functionally Substituted Tetraorganotin Derivatives of Acetylenes Functionally Substituted Unsymmetric Tetraorganotin Compounds Tetraorganotin Compounds Containing Halogen Tetraorganotin Compounds Containing Pseudohalogen Groups Unsymmetric Tetraorganotin Compounds Containing Oxygen Compounds Derived from a Hydroxy Group Peroxy Tetraorganotin Compounds Organotin Compounds Containing Carbonyl Groups Tetraorganotin Compounds Containing Carboxyl Groups Tetraorganotin Compounds Containing Sulfur Tetraorganotin Compounds Containing Nitrogen »2 Tetraorganotin Compounds Containing Phosphorous Tetraorganotin Compounds Containing Organometallic Substituents Bridged Organotin Compounds Tetraorganotin Compounds with Organosilyl Substituents Tetraorganotin Compounds with Organogermanium Substituents 248 XIII

5 Tetraorganotin Compounds with Organolead Substituents 248 Tetraorganotin Compounds with Boron and Aluminuni 252 Tetraorganotin Compounds with Group II Metals 252 Tetraorganotin Compounds with Group 1 Metals 254 Tetraorganotin Compounds with Tin-Carbon Double Bonds 254 Organotin Hydrides 254 Nonfunctional Organotin Hydrides 255 Organotin Deuterides 265 Functlonally Substituted Organotin Hydrides 2Ö5 Organotin Hydrides Containing Heteroatom-Tin Bonds 265 Organotin Compounds Containing Heteroatom-Tin Bonds Organotin Halides 268 Triorganotin Halides 268 Symmetrie Unsubstituted Triorganotin Halides 268 Unsymmetric Unsubstituted Triorganotin Halides 286 Heterocyclic Substituted Triorganotin Halides 290 Unsaturated Triorganotin Halides 290 Furictionally Substituted Triorganotin Halides 290 Halogen-Substituted Triorganotin Halides 290 Pseudohalogen-Substituted Triorganotin Halides 290 Oxygen-Containing Triorganotin Halides 290 Nitrogen-Substituted Triorganotin Halides 290 Metal-Substituted Triorganotin Halides 290 Diorganotin Dihalides 502 Unsubstituted Diorganotin Dihalides 302 Heterocyclic Substituted Diorganotin Dihalides 515 Unsaturated Diorganotin Dihalides 521 Functionally Substituted Diorganotin Dihalides 522 Halogen-Substituted Diorganotin Dihalides 522 Pseudohalogen-Substituted Diorganotin Dihalides 322 Oxygen-Substituted Diorganotin Dihalides 522 Diorganotin Dihalides Containing Nitrogen or Silicon 522 Organotin Trihalides 327 Unsubstituted Organotin Trihalides 328 Heterocyclic Organotin Trihalides 333 Unsaturated Organotin Trihalides 333 Functionally Substituted Organotin Trihalides 355 Halogen-Substituted Organotin Trihalides 333 Organotin Trihalides with Substituents Other Than Halogen 353 Organotin Halides Containing Tin-Oxygen Bonds 356 Organotin Halides Containing Oxy- or Hydroxy-Groups 557 Organotin Halides Containing Alkoxy Groups 337 Organotin Halides Containing Carboxylate Groups 342 Organotin Halides Containing Tin-Sulfur Bonds 342 Organotin Salts Organotin Pseudohalides Organotin Salts or Esters of Oxygen Acids 347 XIV

6 Organotin Oxygen Compounds 358,1 Organotin Oxides and Hydroxides 358,1.1 Triorganotin Oxides and Hydroxides Diorganotin Oxides and Hydroxides 3^7 2.1 Nonfunctionally Substituted Diorganotin Oxides and Hydroxides 3ÖT 2.6 Functionally Substituted Diorganotin Oxides and Hydroxides Monoorganotin Oxides and Hydroxides 375 Organotin Peroxy Compounds 378 Organotin Alkoxides Triorganotin Alkoxides and Phenoxides Triorganotin Alkoxides Derived from Heterocyclic Alcohols 383 l.k Triorganotin Alkoxides Derived from Unsaturated Alcohols Triorganotin Alkoxides Derived from Functionally Substituted Alcohols Triorganotin Alkoxides Derived from Halogen-Substituted Phenols Triorganotin Alkoxides Derived from Alcohols or Phenols Containing Oxygen Functions Triorganotin Alkoxides Derived from Alcohols or Phenols Containing Nitrogen Triorganotin Alkoxides Derived from Organometallic Substituted Alcohols or Phenols Triorganotin Mixed Oxides Diorganotin Alkoxides Unsubstituted Diorganotin Alkoxides and Phenoxides Diorganotin Alkoxides Derived from Heterocyclic Alcohols Diorganotin Alkoxides Derived from Functionally Substituted Alcohols and Phenols Diorganotin Alkoxides Derived from Halogen-Substituted Phenols Diorganotin Alkoxides Derived from Alcohols or Phenols Containing Oxygen Functions Diorganotin Alkoxides Derived from Alcohols or Phenols Containing Nitrogen Diorganotin Alkoxides Derived from Dihydric Alcohols or Phenols Miscellaneous Diorganotin Alkoxides Diorganotin Siloxanes Diorganotin Alkoxide Carboxylates Monoorganotin Trialkoxides ko8.k Organotin Derivatives of Acetals ko8 5 Organotin Carboxylates 4o8 5-1 Triorganotin Carboxylates koö XV

7 k.$.$.1.1 Unsubstituted Triorganotin Carboxylates Unsubstituted Triorganotin Carboxylates Derived from Heterocyclic Acids Unsubstituted Triorganotin Carboxylates Derived from Unsaturated Acids I.6 Unsubstituted Triorganotin Carboxylates Derived from Functionally Substituted Acids Unsubstituted Triorganotin Carboxylates Derived from Halogen-Substituted Acids Unsubstituted Triorganotin Carboxylates Derived from Oxygen- and Sulfur-Containing Acids I.6.5 Unsubstituted Triorganotin Carboxylates Derived from Acids Containing Nitrogen Unsubstituted Triorganotin Carboxylates Derived from Acids Containing Mercury »1.6.8 Unsubstituted Triorganotin Carboxylates Derived from Polyfunctional Acids I.6.8.I Bis-Triorganotin Derivatives of Dicarboxylic Acids Unsubstituted Triorganotin Carboxylates Derived from Polyfunctional Acids Unsymmetric or Functionally Substituted Triorganotin Carboxylates Unsymmetric Triorganotin Carboxylates > Unsymmetric Triorganotin Carboxylates Derived from Functionally Substituted Acids I.9.3 Functionally Substituted Triorganotin Carboxylates Diorganotin Carboxylates Unsubstituted Diorganotin Carboxylates Diorganotin Derivatives of Heterocyclic and Unsaturated Carboxylic Acids Functionally Substituted Diorganotin Carboxylates Halogen-Substituted Diorganotin Carboxylates Diorganotin Carboxylates Derived from Acids Substituted with Oxygen, Sulfur, Nitrogen, and Phosphorous Diorganotin Carboxylates of Dicarboxylic Acids Diorganotin Carboxylates Containing Tin-Sulfur Bonds 446 ^ Monoorganotin Carboxylates Organotin Compounds with Sulfur, Selenium, and Tellurium Organotin Sulfides, Selenides, and Tellurides Triorganotin Sulfides, Selenides, and Tellurides Diorganotin Sulfides, Selenides, and Tellurides Monoorganotin Sulfides and Selenides Organotin Mercaptides and Organoselenides Triorganotin Mercaptides Unsubstituted Triorganotin Mercaptides and Organoselenides Heterocyclic Substituted Triorganotin Mercaptides Functionally Substituted Triorganotin Mercaptides 456 XVI

8 Diorganotin Dimercaptides Unsubstituted Diorganotin Dimercaptides Heterocyclic Substituted Diorganotin Dimercaptides Functionally Substituted Diorganotin Dimercaptides Monoorganotin Trimercaptides Organotin Thiocarboxylates, Xanthates, and Thiocarbatnates Metal-Substituted Organotin Sulfides, Selenides, and Tellurides Organotin Compounds with Nitrogen, Phosphorous, Arsenic, Antimony, and Bismuth Unsubstituted Organotin Amides, Imides, and Nitrides Heterocyclic Organotin Imides Organotin Derivatives of Acid Amides and Acid Imides Organotin Metal Imides Organotin Imido Phosphoranes and Imido Stibanes Organotin Phosphides, Arsenides, Antimonides, and Bismuthides Organo-Polytin Compounds 5.1 Hexaorganoditin Compounds Organo-Polytin Compounds Containing More Than Two Tin Atoms Organo-Polytin Halides Organo-Polytin Carboxylates Bimetallic Organotin Compounds 6.1 Organotin Derivatives of Groups II-IV Elements Organotin Alkali Metal Compounds Organotin Derivatives with Transition Metal Coordination Compounds Cyclic Organotin Compounds 7.1 Cyclic Tetraorganotin Compounds Cyclic Organotin Compounds with Heteroatom-Tin Bonds Cyclic Organo-Polytin Compounds Miscellaneous Organotin Compounds 8.1 Polymerization Reactions with Organotin Compounds Unspecified Organotin Compounds Commercial Application of Organotin Compounds 515 LEAD 1. Symmetrie Tetraorganolead Compounds 1.1 Unsubstituted Tetraorganolead Compounds Symmetrie Tetraheterocyclic Lead Compounds Symmetrie Unsaturated Tetraorganolead Compounds Functionally Substituted Symmetrie Tetraorganolead Compounds 530 XVII

9 2. Unsymmetric Tetraorganolead Compounds 2.1 Nonfunctional Tetraorganolead Compounds Heterocyclic Substituted Tetraorganolead Compounds Tetraorganolead Compounds with Olefinic Substituents Tetraorganolead Compounds with Acetylenic Substituents Functionally Substituted Tetraorganolead Compounds 54l Tetraorganolead Compounds Containing Halogen 54l Tetraorganolead Compounds Containing Oxygen )- Tetraorganolead Compounds Containing Sulfur 54l Tetraorganolead Compounds Containing Nitrogen Metal-Substituted Tetraorganolead Compounds 5^ Bridged Tetraorganolead Compounds 5^ Tetraorganolead Compounds with Metallic Substituents Organolead Hydrides Organolead Compounds Containing Heteroatom-Lead Bonds 4.1 Organolead Halides Trlorganolead Halides Unsubstituted Triorganolead Halides Heterocyclic Triorganolead Halides Unsaturated Triorganolead Halides Functionally Substituted Triorganolead Halides Diorganolead Dihalides Unsubstituted Diorganolead Dihalides Substituted Diorganolead Dihalides 56l Monoorganolead Halides Organolead Salts 5Ö Organolead Pseudohalides Organolead Salts or Esters of Oxygen Acids Organolead Oxygen Compounds Organolead Oxides and Hydroxides Organolead Peroxides Organolead Alkoxides Organolead Siloxanes Organolead Carboxylates *1 Triorganolead Carboxylates «1 Triorganolead Carboxylates Derived from Unsubstituted Acids Triorganolead Carboxylates Derived from Heterocyclic Acids «1-4 Triorganolead Carboxylates Derived from Unsaturated Acids Triorganolead Carboxylates Derived from Functionally Substituted Acids Triorganolead Carboxylates Derived from Halogen- Containing Acids «1.6.3 Triorganolead Carboxylates Derived from Oxygen- and Nitrogen-Substituted Acids 573 XVIII

10 Diorganolead Carboxylates Diorganolead Carboxylates Derived from Unsubstituted Acids *2.2 Diorganolead Dicarboxylates Derived from Substituted Acids Monoorganolead Tricarboxylates Organolead Compounds with Sulfur, Selenium, and Tellurium Organolead Compounds with Nitrogen and Phosphorous Organo-Polylead Compounds 5.1 Hexaorganodilead Compounds Organolead Compounds with Less Than Three Organic Groups per Lead Atom Bimetallic Organolead Compounds 6.1 Organolead Derivatives of Groups I-IV Metals Organolead Derivatives with Transition Metal Coordination Compounds Cyclic Organolead Compounds Miscellaneous Organolead Compounds 8.1 Polymerization Reactions with Organolead Compounds Unspecified Organolead Compounds 598 BIBLIOGRAPHY 599 REVIEW PUBLICATIONS AND MONOGRAPHS 691 XIX