Organic synthesis on solid phase : supports, linkers, reactions / Florencio Zaragoza Dorwald.

By: Dörwald, Florencio Zaragoza .

Material type: materialTypeLabel

BookPublisher: Weinheim : Wiley-VCH, 2000Description: vi, 474 p. : ill. ; 25 cm + hbk.ISBN: 3527299505.Subject(s): Organic compounds -- Synthesis

| Solid-phase synthesis

DDC classification: 547.2

Contents:

General techniques and analytical tools for solid-phase organic synthesis -- Supports for solid-phase organic synthesis -- Linkers for solid-phase organic synthesis -- Preparation of organometallic compounds -- Preparation of hydrocarbons -- Preparation of alkyl and aryl halides -- Preparation of alcohols and ethers -- Preparation of sulfur compounds -- Preparation of organoselenium compounds -- Preparation of nitrogen compounds -- Preparation of phosphorus compounds -- Preparation of aldehydes and ketones -- Preparation of carboxylic acid derivatives -- Preparation of carbonic acid derivatives -- Preparation of heterocycles -- Preparation of oligomeric compounds.

Holdings
Item type	Current library	Call number	Copy number	Status	Date due	Barcode	Item holds
General Lending	MTU Bishopstown Library Lending	547.2 (Browse shelf(Opens below))	1	Available		00077812

Total holds: 0

Enhanced descriptions from Syndetics:

This is the number-one successful book on solid phase organic synthesis, now in its second, expanded edition. It offers the reader

? a comprehensive overview of supports, spacers, and linkers
? 15% more contents
? everything there is to know about reactions and their applications
? clear structure
? numerous experimental guidelines for use in practice

The ideal reference for newcomers and experts.

"... I have no doubts that this text will be the benchmark for future publications on the subject, and a very hard act to follow for authors planning books of their own on this red hot topic."

The Alchemist

Includes bibliographical references and index.

Table of contents provided by Syndetics

Glossary and Abbreviations (p. XIV)
Experimental Procedures (p. XX)
1 General Techniques and Analytical Tools for Solid-Phase Organic Synthesis (p. 1)
1.1 General Techniques for Performing Syntheses on Insoluble Supports (p. 1)
1.2 Strategies for Parallel Synthesis (p. 3)
1.3 Analytical Methods for Support-bound Intermediates (p. 5)
1.3.1 Combustion Analysis (p. 5)
1.3.2 Colorimetric Assays (p. 5)
1.3.3 Infrared Spectroscopy (p. 7)
1.3.4 Mass Spectrometry (p. 7)
1.3.5 Nuclear Magnetic Resonance Spectroscopy (p. 7)
1.4 Strategies for the Selection of Reactions and Reagents for Parallel Solid-Phase Synthesis (p. 8)
2 Supports for Solid-Phase Organic Synthesis (p. 13)
2.1 Polystyrene (p. 14)
2.1.1 Microporous Styrene-Divinylbenzene Copolymers (p. 14)
2.1.1.1 Swelling Behavior (p. 15)
2.1.1.2 Chemical Stability (p. 17)
2.1.1.3 Functionalization (p. 17)
2.1.2 Macroporous Styrene-Divinylbenzene Copolymers (p. 19)
2.1.3 Miscellaneous Polystyrenes (p. 20)
2.2 Poly(ethylene glycol)-Polystyrene Graft Polymers (p. 21)
2.3 Poly(ethylene glycol) (p. 22)
2.4 Polyacrylamides (p. 22)
2.5 Polyacrylamide-PEG Copolymers (p. 24)
2.6 Silica (p. 25)
2.7 Polysaccharides (p. 26)
2.8 Miscellaneous Supports (p. 27)
3 Linkers for Solid-Phase Organic Synthesis (p. 33)
3.1 Linkers for Carboxylic Acids (p. 35)
3.1.1 Linkers for Acids Cleavable by Acids or Other Electrophiles (p. 35)
3.1.1.1 Benzyl Alcohol Linkers (p. 35)
3.1.1.2 Diarylmethanol (Benzhydrol) Linkers (p. 37)
3.1.1.3 Trityl Alcohol Linkers (p. 37)
3.1.1.4 Non-Benzylic Alcohol Linkers (p. 38)
3.1.2 Linkers for Acids Cleavable by Bases or Nucleophiles (p. 39)
3.1.2.1 Benzyl Alcohol Linkers (p. 40)
3.1.2.2 Non-Benzylic Alcohol Linkers (p. 40)
3.1.2.3 Miscellaneous Linkers Cleavable by Bases or Nucleophiles (p. 43)
3.1.3 Photocleavable Linkers for Carboxylic Acids (p. 45)
3.1.4 Linkers for Acids Cleavable by Transition Metal Catalysis (p. 47)
3.1.5 Linkers for Acids Cleavable by Enzymes (p. 49)
3.2 Linkers for Thiocarboxylic Acids (p. 50)
3.3 Linkers for Amides, Sulfonamides, Carbamates, and Ureas (p. 50)
3.3.1 Benzylamine Linkers (p. 51)
3.3.2 (Diarylmethyl)amine and Tritylamine Linkers (p. 55)
3.3.3 Linkers for Amides Cleavable by Nucleophiles (p. 59)
3.3.3.1 Nucleophilic Cleavage of Alkyl Esters (p. 59)
3.3.3.2 Nucleophilic Cleavage of Aryl Esters (p. 61)
3.3.3.3 Nucleophilic Cleavage of Oxime and Related Esters (p. 63)
3.3.3.4 Nucleophilic Cleavage of Amides and Carbamates (p. 63)
3.4 Linkers for Hydroxamine Acids and Hydrazides (p. 63)
3.5 Linkers for Carboxylic Esters (p. 67)
3.5.1 Linkers for Esters Cleavable by Nucleophiles (p. 67)
3.5.2 Linkers for Lactones Cleavable by Electrophiles or Oxidants (p. 70)
3.6 Linkers for Primary and Secondary Aliphatic Amines (p. 71)
3.6.1 Benzylamine, (Diarylmethyl)amine, and Tritylamine Linkers (p. 72)
3.6.2 Carbamate Attachment (p. 74)
3.6.3 Miscellaneous Linkers for Aliphatic Amines (p. 76)
3.7 Linkers for Tertiary Amines (p. 77)
3.8 Linkers for Aryl- and Heteroarylamines (p. 79)
3.9 Linkers for Guanidines and Amidines (p. 81)
3.10 Linkers for Pyrroles, Imidazoles, Triazoles, and Tetrazoles (p. 84)
3.11 Linkers for Alcohols and Phenols (p. 85)
3.11.1 Attachment as Ethers (p. 85)
3.11.2 Attachment as Silyl Ethers (p. 89)
3.11.3 Attachment as Acetals (p. 91)
3.11.4 Attachment as Esters (p. 91)
3.11.5 Miscellaneous Linkers for Alcohols and Phenols (p. 94)
3.12 Linkers for Thiols (p. 96)
3.13 Linkers for Alkyl and Aryl Halides (p. 99)
3.14 Linkers for Aldehydes and Ketones (p. 99)
3.14.1 Attachment as Enol Ethers, Enamines, and Imines (p. 100)
3.14.2 Attachment of Carbonyl Compounds as Acetals (p. 100)
3.14.3 Miscellaneous Linkers for Aldehydes and Ketones (p. 103)
3.15 Linkers for Olefins (p. 103)
3.15.1 Linkers for Olefins Cleavable by [beta]-Elimination (p. 104)
3.15.2 Linkers for Olefins Cleavable by Olefin Metathesis (p. 108)
3.16 Linkers for Alkanes and Arenes (p. 110)
3.16.1 Cleavage followed by Decarboxylation (p. 110)
3.16.2 Cleavage of Silanes and related Compounds (p. 111)
3.16.3 Reductive Cleavage of Carbon-Oxygen and Carbon-Nitrogen Bonds (p. 114)
3.16.4 Reductive Cleavage of Carbon-Phosphorus, Carbon-Sulfur, and Carbon-Selenium Bonds (p. 116)
3.17 Non-Covalent Linkers (p. 118)
3.17.1 Ion-Exchange Resins (p. 118)
3.17.2 Transition Metal Complexes (p. 118)
3.17.3 Miscellaneous Non-Covalent Linkers (p. 119)
4 Preparation of Organometallic Compounds (p. 133)
4.1 Group I and II Organometallic Compounds (p. 133)
4.2 Group III Organometallic Compounds (p. 136)
4.3 Group IV Organometallic Compounds (p. 137)
4.4 Transition Metal Complexes (p. 138)
5 Preparation of Hydrocarbons (p. 143)
5.1 Preparation of Alkanes (p. 143)
5.1.1 Preparation of Alkanes by Hydrolysis of Organometallic Compounds (p. 143)
5.1.2 Preparation of Alkanes by Hydrogenation and Reduction (p. 143)
5.1.3 Preparation of Alkanes by Carbon-Carbon Bond Formation (p. 145)
5.1.3.1 Coupling Reactions with Group I Organometallic Compounds (p. 145)
5.1.3.2 Coupling Reactions with Group II Organometallic Compounds (p. 146)
5.1.3.3 Coupling Reactions with Boranes (p. 147)
5.1.3.4 Coupling Reactions with Arylpalladium Compounds (p. 148)
5.1.3.5 Alkylations with Alkyl Radicals (p. 149)
5.1.3.6 Preparation of Cycloalkanes (p. 150)
5.2 Preparation of Alkenes (p. 151)
5.2.1 Preparation of Alkenes by [beta]-Elimination and Reduction (p. 151)
5.2.2 Preparation of Alkenes by Carbonyl Olefination (p. 152)
5.2.2.1 By Wittig Reaction (p. 152)
5.2.2.2 By Aldol and Related Condensations (p. 155)
5.2.2.3 By Other Carbonyl Olefinations (p. 156)
5.2.3 Preparation of Alkenes by Olefin Metathesis (p. 156)
5.2.4 Preparation of Alkenes by C-Vinylation (p. 159)
5.2.5 Preparation of Cycloalkenes by Cycloaddition (p. 163)
5.3 Preparation of Alkynes (p. 165)
5.4 Preparation of Biaryls (p. 168)
6 Preparation of Alkyl and Aryl Halides (p. 177)
6.1 Preparation of Alkyl Halides (p. 177)
6.2 Preparation of Aryl and Heteroaryl Halides (p. 181)
7 Preparation of Alcohols and Ethers (p. 185)
7.1 Preparation of Alcohols (p. 186)
7.1.1 Reduction of Carbonyl Compounds (p. 186)
7.1.2 Addition of Carbon Nucleophiles to C-O Double Bonds (p. 187)
7.1.3 Miscellaneous Preparations of Alcohols (p. 191)
7.1.4 Protective Groups for Alcohols (p. 193)
7.1.4.1 Protective Groups Cleavable by Acids (p. 193)
7.1.4.2 Protective Groups Cleavable by Nucleophiles (p. 195)
7.2 Preparation of Ethers (p. 197)
7.2.1 Preparation of Dialkyl Ethers (p. 197)
7.2.2 Preparation of Alkyl Aryl Ethers (p. 200)
7.2.3 Preparation of Diaryl Ethers (p. 204)
8 Preparation of Sulfur Compounds (p. 209)
8.1 Preparation of Thiols (p. 209)
8.2 Preparation of Thioethers (p. 211)
8.3 Preparation of Sulfoxides and Sulfones (p. 215)
8.4 Preparation of Sulfonamides (p. 216)
8.5 Preparation of Sulfonic Esters (p. 221)
9 Preparation of Organoselenium Compounds (p. 227)
10 Preparation of Nitrogen Compounds (p. 229)
10.1 Preparation of Amines (p. 229)
10.1.1 Preparation of Amines by Aliphatic Nucleophilic Substitution (p. 229)
10.1.1.1 With Support-Bound Alkylating Agents (p. 229)
10.1.1.2 By Alkylation of Support-Bound Amines (p. 233)
10.1.2 Preparation of Amines by Aromatic Nucleophilic Substitution (p. 233)
10.1.2.1 With Support-Bound Arylating Agents (p. 233)
10.1.2.2 By Arylation of Support-Bound Amines (p. 237)
10.1.3 Preparation of Amines by Addition of Amines to C-C Double Bonds (p. 239)
10.1.4 Preparation of Amines by Reduction of Imines (p. 239)
10.1.5 Preparation of Amines by Reaction of Carbon Nucleophiles with Imines or Aminals (p. 242)
10.1.6 Preparation of Amines by Reduction of Amides and Carbamates (p. 245)
10.1.7 Preparation of Amines by Reduction of Nitro Compounds (p. 246)
10.1.8 Preparation of Amines by Reduction of Azides (p. 247)
10.1.9 Miscellaneous Preparations of Amines (p. 248)
10.1.10 Protective Groups for Amines (p. 249)
10.1.10.1 Carbamates (p. 250)
10.1.10.2 Amides (p. 256)
10.1.10.3 Cyclic Imides (p. 257)
10.1.10.4 Enamines (p. 258)
10.1.10.5 Imines (p. 259)
10.1.10.6 N-Alkyl and N-Aryl Derivatives (p. 259)
10.1.10.7 N-Sulfenyl and N-Sulfonyl Derivatives (p. 260)
10.2 Preparation of Quaternary Ammonium Salts (p. 261)
10.3 Preparation of Hydrazines and Hydroxylamines (p. 262)
10.4 Preparation of Azides (p. 263)
10.5 Preparation of Diazo Compounds (p. 264)
10.6 Preparation of Nitro Compounds (p. 265)
11 Preparation of Phosphorus Compounds (p. 274)
11.1 Phosphonic Acid Derivatives (p. 274)
12 Preparation of Aldehydes and Ketones (p. 275)
12.1 Preparation of Aldehydes and Ketones by C-Acylation (p. 275)
12.2 Preparation of Aldehydes and Ketones by Oxidation (p. 277)
12.3 Miscellaneous Preparations of Aldehydes and Ketones (p. 278)
13 Preparation of Carboxylic Acid Derivatives (p. 285)
13.1 Preparation of Amides (p. 285)
13.1.1 Preparation of Amides by Acylation of Amines with Isolated Acylating Agents (p. 285)
13.1.2 Acylation of Amines with Acylating Reagents Formed In Situ (p. 288)
13.1.2.1 Activation of Acids with Carbodiimides (p. 290)
13.1.2.2 Activation of Acids with Phosphonium Salts (p. 294)
13.1.2.3 Activation of Acids with Uronium Salts (p. 296)
13.1.3 Miscellaneous Preparations of Amides (p. 298)
13.1.4 Preparation of Amides by C-Alkylation of Other Amides (p. 300)
13.1.5 Preparation of Amides by N-Alkylation of Other Amides (p. 301)
13.2 Preparation of Hydroxamic Acids and Hydrazides (p. 302)
13.3 Preparation of Carboxylic Acids (p. 303)
13.4 Preparation of Carboxylic Esters (p. 304)
13.4.1 Preparation of Esters from Support-Bound Alcohols (p. 304)
13.4.1.1 Esterification of Support-bound Alcohols with N-Protected [alpha]-Amino Acids (p. 309)
13.4.2 Preparation of Esters from Support-Bound Alkylating Agents (p. 311)
13.4.3 Preparation of Esters from Support-Bound Carboxylic Acids (p. 313)
13.4.4 Preparation of Esters by Chemical Modification of Other Esters (p. 315)
13.5 Preparation of Thiol Esters (p. 315)
13.6 Preparation of Amidines and Imino Ethers (p. 315)
13.7 Preparation of Nitriles and Isonitriles (p. 318)
13.8 Preparation of Imides (p. 319)
13.9 Preparation of Thioamides (p. 321)
14 Preparation of Carbonic Acid Derivatives (p. 327)
14.1 Preparation of Carbodiimides (p. 327)
14.2 Preparation of Isocyanates and Isothiocyanates (p. 328)
14.3 Preparation of Guanidines (p. 329)
14.4 Preparation of Ureas (p. 331)
14.5 Preparation of Thioureas and Isothioureas (p. 334)
14.6 Preparation of Carbamates (p. 335)
14.7 Preparation of Carbonates and Miscellaneous Carbonic Acid Derivatives (p. 338)
15 Preparation of Heterocycles (p. 343)
15.1 Preparation of Epoxides and Aziridines (p. 343)
15.2 Preparation of Azetidines and Thiazetidines (p. 344)
15.3 Preparation of Pyrroles and Pyrrolidines (p. 345)
15.4 Preparation of Indoles and Indolines (p. 350)
15.5 Preparation of Furans and Tetrahydrofurans (p. 354)
15.6 Preparation of Benzofurans and Dihydrobenzofurans (p. 356)
15.7 Preparation of Thiophenes (p. 358)
15.8 Preparation of Imidazoles (p. 361)
15.9 Preparation of Hydantoins (2,4-Imidazolidinediones) and Thiohydantoins (p. 363)
15.10 Preparation of Benzimidazoles (p. 367)
15.11 Preparation of Isoxazoles (p. 369)
15.12 Preparation of Oxazoles and Oxazolidines (p. 373)
15.13 Preparation of Thiazoles and Thiazolidines (p. 373)
15.14 Preparation of Pyrazoles (p. 374)
15.15 Preparation of Triazoles, Tetrazoles, Oxadiazoles, and Thiadiazoles (p. 376)
15.16 Preparation of Pyridines and Dihydropyridines (p. 378)
15.17 Preparation of Tetrahydropyridines and Piperidines (p. 380)
15.18 Preparation of Fused Pyridines (p. 382)
15.19 Preparation of Pyridazines (1,2-Diazines) (p. 387)
15.20 Preparation of Pyrimidines (1,3-Diazines) (p. 389)
15.21 Preparation of Quinazolines (p. 391)
15.22 Preparation of Pyrazines and Piperazines (1,4-Diazines), and Fused Derivatives thereof (p. 394)
15.22.1 Preparation of Diketopiperazines (p. 394)
15.22.2 Preparation of Miscellaneous 1,4-Diazines and Quinoxalines (p. 397)
15.23 Preparation of Triazines (p. 398)
15.24 Preparation of Pyrans and Benzopyrans (p. 399)
15.25 Preparation of Oxazines and Thiazines (p. 400)
15.26 Preparation of Azepines and Larger Heterocycles with one Nitrogen Atom (p. 402)
15.27 Preparation of Diazepines, Thiazepines, and larger Heterocycles with more than one Heteroatom (p. 404)
16 Preparation of Oligomeric Compounds (p. 413)
16.1 Peptides (p. 414)
16.1.1 Merrifield's Peptide Synthesis (p. 414)
16.1.2 The Boc Strategy (p. 415)
16.1.3 The Fmoc Strategy (p. 417)
16.1.4 Side-Chain Protection (p. 419)
16.1.5 Backbone Protection (p. 420)
16.1.6 Cyclic Peptides (p. 421)
16.2 Oligonucleotides (p. 422)
16.2.1 Historical Overview (p. 422)
16.2.2 The Phosphotriester Method (p. 424)
16.2.3 The Phosphoramidite and H-Phosphonate Methods (p. 425)
16.2.4 Oligonucleotide Analogs (p. 428)
16.3 Oligosaccharides (p. 428)
16.3.1 Glycosylation with Glycosyl Bromides (p. 429)
16.3.2 Glycosylation with Glycosyl Sulfoxides (p. 430)
16.3.3 Glycosylation with Glycosyl Thioethers (p. 431)
16.3.4 Glycosylation with Miscellaneous Glycosyl Donors (p. 431)
16.4 Miscellaneous Oligomeric Compounds (p. 433)
16.4.1 Oligoamides (p. 433)
16.4.1.1 Oligoglycines (p. 434)
16.4.1.2 Peptide Nucleic Acids (PNA) (p. 434)
16.4.2 Oligoesters (p. 436)
16.4.3 Oligoureas and Oligothioureas (p. 436)
16.4.4 Oligocarbamates (p. 437)
16.4.5 Oligosulfonamides (p. 438)
16.4.6 Oligomeric Phosphoric Acid Derivatives (p. 438)
16.4.7 Peptide-Derived Oligomeric Compounds (p. 439)
16.4.8 Oligomers Prepared by C-C Bond Formation (p. 439)
16.4.9 Dendrimers (p. 441)
17 Index (p. 449)

Organic synthesis on solid phase : supports, linkers, reactions / Florencio Zaragoza Dorwald.

By: Dörwald, Florencio Zaragoza.

Enhanced descriptions from Syndetics:

Table of contents provided by Syndetics

By: Dörwald, Florencio Zaragoza .