Organic Syntheses, Collective Volume 6

Contains the procedures previously published in annual volumes 50–59, revised and updated where necessary. Efforts have been made to standardize the style of experimental procedures and the presentation of spectroscopic data. Increasing emphasis on the toxicology of organic compounds has led to the inclusion of additional hazard warnings, particularly for benzene, hexamethylphosphoric triamide (HMPA), and methyl iodide at the many places where they appear. Some experimental procedures have been improved, references have been added, and the index has been greatly expanded and simultaneously consolidated for efficient and easy use.

Spis treści:
[The numbers in parentheses refer to the annual volume (in boldface type) and page number where each procedure first appeared]
Acylamidoalkyl Acetophenones from Substituted Phenethylamines: 2–(2–Acetamidoethyl)–4,5–dimethoxyacetophenone … (56, 3)
Thiol Protection with the Acetamidomethyl Group: S–Acetamidomethyl–l–cysteine Hydrochloride … (59, 190)
Acetic Formic Anhydride … (50, 1)
Acetone Hydrazone … (50, 3)
Preparation of Hydrazones: Acetophenone Hydrazone … (50, 102)
3β–Acetoxy–5α–cyanocholestan–7–one … (52, 100)
p–Acetyl–α–bromohydrocinnamic Acid … (51, 1)
α,β–Dehydrogenation of β–Dicarbonyl Compounds by Selenoxide Elimination: 2–Acetyl–2–cyclohexen–1–one … (59, 58)
2–Acetyl–1,3–cyclopentanedione … (52, 1)
3–Acetyl–2,4–dimethylfuran … (53, 1)
2–Acetyl–6–methoxynaphthalene … (53, 5)
Copper Catalyzed Arylation of β–Dicarbonyl Compounds: 2–(1–Acetyl–2–oxopropyl)benzoic Acid … (58, 52)
5–Acetyl– 1,2,3,4,5–pe ntamethylcyclopentadiene … (56, 1)
2–Adamantanecarbonitrile … (57, 8)
Tertiary Alcohols from Hydrocarbons by Ozonation on Silica Gel: 1–Adamantanol … (59, 176)
Adamantanone … (53, 8)
Enone Reduction–Enolate Alkylation Sequence: 2–Allyl–3–methylcyclohexanone … (56, 52)
Preparation of N–Aminoaziridines: trans–1–Amino–2,3–diphenylaziridine, 1–Amino–2–phenylaziridine, and 1–Amino–2–phenylaziridinium Acetate … (55, 114)
Reduction of Ketones by Use of the Tosylhydrazone Derivatives: Androstan–17β–Ol … (52, 122)
Aldehydes from 4,4–Dimethyl–2–oxazoline and Grignard Reagents: o–Anisaldehyde … (54, 42)
[18]Annulene … (54, 1)
Azetidine … (53, 13)
Azoethane … (52, 11)
Diels–Alder Addition of Perchlorobenzyne: Benzobarrelene … (59, 71)
Benzocyclopropene … (55, 12)
α–Chlorination of Carboxylic Acids Mediated by Chlorosulfonic Acid: &phis;–Benzoylamino–α–chlorocaproic Acid … (59, 20)
1–N–Acylamino–1,3–dienes from 2,4–pentadienoic Acids by the Curtius Rearrangement: Benzyl trans–1,3–Butadiene–1–carbamate … (59, 1)
Benzyl Chloromethyl Ether … (52, 16)
1–Benzylindole … (54, 58)
N–Alkylindoles from the Alkylation of Sodium Indolide in Hexamethylphosphoric Triamide: 1–Benzylindole … (54, 60)
3–Alkylated and 3–Acylated Indoles from a Common Precursor: 3–Benzylindole and 3–Benzoylindole … (56, 8)
Alkylation of Isoquinolines via 2–Benzoyl–1,2–dihydroisoquinaldonitriles: 1–Benzylisoquinoline … (56, 19)
The Formation and Alkylation of Specific Enolate Anions from an Unsymmetrical Ketone: 2–Benzyl–2–m ethylcyclohexanone and 2–Benzyl–6–methylcyclohexanone … (52, 39)
Sulfide Synthesis: Benzyl Sulfide … (58, 138)
Bicyclo[1.1.0]butane … (51, 55)
Boranes in Functionalization of Dienes to Cyclic Ketones: Bicyclo[3.3.1]nonan–9–one … (58, 24)
Bicyclo[3.2.1]octan–3–one … (51, 60)
Bicyclo[2.1.0]pent–2–ene … (55, 15)
Dehydroxylation of Phenols; Hydrogenolysis of Phenolic Ethers: Biphenyl … (51, 82)
Controlled–Potential Electrolytic Reduction: 1,1–Bis(bromomethyl)cyclopropane … (52, 22)
Bis(trifluoromethyl)diazomethane … (50, 6)
Bis[2,2,2–trifluoro–1–phenyl–1–(trifluoromethyl)ethoxy] Diphenyl Sulfurane … (57, 22)
Acyloin Condensation in which Chlorotrimethylsilane is Used as a Trapping Agent: 1,2–Bis(trimethylsilyloxy)cyclobutene and 2–Hydroxycyclobutanone … (57, 1)
2–Bornene … (51, 66)
Selective α–Bromination of an Aralkyl Ketone with Phenyltrimethylammonium Tribromide: 2–Bromoacetyl–6–methoxynaphthalene and 2,2–Dibromoacetyl–6–methoxynaphthalene … (53, 111)
Mercury(II) Oxide–Modified Hunsdiecker Reaction: 1–Bromo–3–chlorocyclobutane … (51, 106)
para–Bromination of Aromatic Amines: 4–Bromo–N,N–dimethyl–3–(trifluoromethyl)aniline … (55, 20)
Bromohydrins from Alkenes and N–Bromosuccinimide in Dimethyl Sulfoxide; erythro–2–Bromo–1,2–diphenylethanol … (59, 16)
Chain Elongation of Alkenes via gem–Dihalocyclopropanes: 2–Bromo–3,3–diphenyl–2–propen–1–yl acetate … (56, 32)
2–Bromohexanoyl Chloride … (55, 27)
1–Bromo–3–methyl–2–butanone … (55, 24)
trans, trans–1,3–Butadiene–1,4R 11;diyl Diacetate … (50, 24)
A New Reagent for tert–Butoxycarbonylation: 2–tert–Butoxycarbonyloxyimino–2–phenylacetonitrile … (59, 95)
tert–Butoxycarbonyl–l–proline … (53, 25)
tert–Butyl Azidoformate … (50, 9; 57, 122)
tert–Butylcyanoketene … (55, 32)
cis–4–tert–Butylcyclohexanol … (50, 13)
Polymeric Carbodiimide. Moffat Oxidation: 4–tert–Butylcyclohexanone … (56, 99)
Oxidation of Alcohols by Methyl Sulfide– N–Chlorosuccinimide– Triethylamine: 4–tert–Butylcyclohexanone … (58, 122)
2–tert–Butyl–1,3–diaminopropane … (53, 21)
Photochemical Ring–Contraction of 2–Ethoxypyrrolin–5–ones to Cyclopropanone Derivatives: tert–Butyl N–(1–Ethoxycyclopropyl)carbamate … (59, 132)
Phase–Transfer Hofmann Carbylamine Reaction: tert–Butyl Isocyanide … (55, 96)
Sulfide Synthesis in Preparation of Unsymmetrical Dlalkyl Disulfides: sec–Butyl Isopropyl Disulfide … (58, 147)
3–Butyl–2–Methylhept–1–en–3–ol … (52, 19)
Monoalkylation of α,β–Unsaturated Ketones via Metalloenamines: 1–Butyl–10–methyl–Δ1(9)–2–octalone (57, 69)
β–Diketones from Methyl Alkyl Ketones: 3–n–Butyl–2,4–pentanedione … (51, 90)
Secondary and Tertiary Alkyl Ketones from Carboxylic Acid Chlorides and Lithium Phenylthio(alkyl)cuprate Reagents: tert–Butyl Phenyl Ketone … (55, 122)
Removal of Nα–Benzyloxycarbonyl Groups from Sulfur–Containing Peptides by Catalytic Hydrogenation in Liquid ammonia: O–tert–Butyl–L–seryl–S–tert–butyl–l–cysteine tert–B