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Organic syntheses vol 58 - Sheppard W.A.

Sheppard W.A., Buchi G.H. Organic syntheses vol 58 - Wiley, 1978. - 123 p.
Download (direct link): organicsynthesesvol581978.pdf
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The Editor-in-Chief wishes to acknowledge a number of people for their efforts on behalf of Organic Syntheses. First, I would like to acknowledge the submitters who have generously agreed to openly share their experimental expertise in the precise manner required by Organic Syntheses and who have patiently borne with us during the checking and editing process. My colleagues on the Board of Editors and their collaborators have checked many of the procedures included in this volume. I would like to take this opportunity to warmly thank my own co-workers for sharing with me a belief in the importance of this work and for contributing their laboratory efforts to this and other volumes of Organic Syntheses.
Professor Wayland Noland, Secretary to the Board, has continued to provide the extensive coordination required in the
PREFACE
XXV
preparation of a volume such as this. Special thanks must be given to Mrs. Rita Seelig Ayers, who, as an expert information chemist, put in long hours checking Chemical Abstracts names and providing very valuable assistance in the final proofing of the manuscript. Finally, but not least, I want to thank my very able secretary, Mrs. Susan S. Wilson, who, with the help of Miss Elizabeth Ann Knipmeyer and Mrs. Mary Wooten, typed the manuscript.
William A. Sheppard
Wilmington, Delaware March 1978
CONTENTS
Ç-Alkyl-I-alkynes Synthesis: 3-Ethyl-1-hexyne............................ 1
ALLYLICALLY TRANSPOSED AMINES FROM ALLYLIC ALCOHOLS: 3,7-DlMETHYL-l,6-
octadien-3-amine........................................................ 4
Arene Oxide Synthesis: Phenanthrene 9, IO-Oxide........................... 12
Bicyclic Ketones for Tropinone Synthesis: 2ol,Aa -Dimethyl-8-oxabicyclo-
[3.2.1]oct-6-en-3-one .................................................... 17
Boranes in Functionalization of Dienes to Cyclic Ketones: Bicyclo-
[3.3.1]nonan-9-one 24
Boranes in Functionalization of Olefins to Amines: 3-Pinanamine............ 32
Carbene Generation by «-Elimination with Lithium 2,2,6,6-Tetramethyl-
piperidide: 1-Ethoxy-2-p-tolylcyclopropane.............................. 37
Catalytic Osmium Tetroxide Oxidation of Olefins: cis-1,2-Cyclohexanediol . 43 Copper Catalyzed Arylation of fj-Dic ariionyl Compounds: 2-(1-Acetyl-2-
oxopropyl)benzoic Acid ................................................. 52
Cyclopentenones from a,a'-DiBROMOKETONES and Enamines: 2,5-Dimethyl-3-
phenyl-2-cyclopenten-1-one ............................................................ 56
cis-Dichloroalkanes from Epoxides: cis - 1,2-Dichlorocyclohexane............... 64
2,3-Dicyanobutadiene as a Reactive Intermediate by in situ Generation from •1,2-DiCYANOCYCLOBUTENE: 2,3-DlCYANO-l,4,4a,9a-TETRAHYDROFLUORENE..... 67
Fluorinations with Pyridinium Polyhydrogen Fluoride Reagent: 1-Fluoro-
adamantane ............................................................ 75
7-Ketoesters from Aldehydes via Diethyl Acylsuccinates: 4-Oxohexanoic
Acid Ethyl Ester........................................................ 79
Y-Ketoesters to Prepare Cyclic Diketones: 2-Methyl-1,3-Cyclopentanf-
dione............................ ........................................ 83
Macrocyclic Polyamines: 1,4,7,10,13,16-Hexaazacyclooctadecane.......... 86
Macrolides from Cyclization of ř-Bromocarboxylic Acids: 11-Hydroxyunde-
canoic Lactone.......................................................... 98
Nitrii.es from Ketones: Cyci.ohf.xanecarbcnitrile........................... 101
Nitrones for Intramolecular 1,3-Dipolar Cycloadditions: Hexahydro-
1,3,3,6-tetramethyl-2,1-benzisoxazoline................................. 106
Nucleophilic a-sec-AMiNOALKYLATiON: 2-(Diphenylhydroxymethyl)pyrrolidine 113 Oxidation of Alcohols by Methyl Sulftoe-JV-Chlorosuccinimide-Triethyl-
AMINE: 4-(er(-BuTYLCYCLOHEX./yNONE........................................ 122
Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents
with Aryl and Alkenyl Halides: 1,2-Dibutylbenzene...................... 127
Radical Anion Arylation: Diethyl Phenylphosphonate..................... 134
Sulfide Synthesis: Benzyl Sulfide .......................................... 138
Sulfide Synthesis in Preparation of Dialkyl and Alkyl Aryl Sulfides: Neopentyl Phenyl Sulfide ...,........................................... 143
xxviii
ORGANIC SYNTHESES—Vol. 58
Sulfide Synthesis in Preparation of Unsymmetrical Dialkyl Disulfides: sec-
Butyl Isopropyl Disulfide ............................................... 147
3-Trimethylsilyl-3-buten-2-one: A Michael Acceptor....................... 152
3-TRIMETHYLSILYL-3-BUTEN-2-ONE AS MlCHAEL ACCEPTOR FOR CONIUGATE Addition-Annelation: cis-4,4a,5,6,7,8-HEXAHYORO-4a,5-DlMETHYL-2(3H)-
NAPHTHALENONE .......................................................... 158
2-Trimethylsilyloxy-1,3-butadiene as a Reactive Diene: Diethyl trans-4-
Trimethylsilyloxy-4-cyclohexene- 1 ,2-dicarboxylate...................... 163
Chemical Hazard Warning ................................................... 168
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