Organic Syntheses, Collective Volume 6

ISBN-13: 9780471852438 / Angielski / Twarda / 1988 / 1232 str.

Wayland E. Noland

Opis

This volume 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.

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)

3 –Acetoxy–5 –cyanocholestan–7–one (52, 100)

p–Acetyl– –bromohydrocinnamic Acid (51, 1)

, –Dehydrogenation of –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 –Dicarbonyl Compounds: 2–(1–Acetyl–2–oxopropyl)benzoic Acid (58, 52)

5–Acetyl– 1,2,3,4,5–pentamethylcyclopentadiene (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–17 –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)

–Chlorination of Carboxylic Acids Mediated by Chlorosulfonic Acid: &phis;–Benzoylamino– –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–methylcyclohexanone 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 –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–1,4–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 , –Unsaturated Ketones via Metalloenamines: 1–Butyl–10–methyl– ¹⁽⁹⁾–2–octalone (57, 69)

–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 N –Benzyloxycarbonyl Groups from Sulfur–Containing Peptides by Catalytic Hydrogenation in Liquid ammonia: O–tert–Butyl–L–seryl–S–tert–butyl–l–cysteine tert–Butyl Ester (59, 159)

Esterification of Hindered Alcohols: tert–Butyl p–Toluate (51, 96)

Peptide Syntheses Using N–Ethyl–5–phenylisoxazolium–3’–sulfonate:

Carbobenzoxy–L–asparaginyl–L–leucine Methyl Ester and N–Carbobenzoxy–3–hydroxy–L–prolylglycylglycine Ethyl Ester (56, 88)

Carbonyl Cyanide (51, 70)

3–Chlorocyclobutanecarboxylic Acid (51, 73)

(z)–4–Chloro–4–hexenyl Trifluoroacetate (57, 26)

m–Chloroperbenzoic Acid (50, 15)

3–(4–Chlorophenyl)–5–(4–Methoxyphenyl)Isoxazole (55, 39)

–Chloro Enamines, Reactive Intermediates for Synthesis: 1–Chloro–N,N,2–trimethylpropenylamine (59, 26)

Modified Clemmensen Reduction: Cholestane (53, 86)

Conjugate Reduction of , –Unsaturated p–Toluenesulfonylhydrazones to Alkenes with Catecholborane: 5 –Cholest–3–ene (59, 42)

5 –Cholest–3–Ene–5–Acetaldehyde (54, 71)

18–Crown–6 (57, 30)

Cinnamonitrile (50, 18)

Preparation of Cyano Compounds Using Alkylaluminum Intermediates: 1–Cyano–6–methoxy–3,4–Dihydronaphthalene (52, 96)

Cyclobutadieneiron Tricarbonyl (50, 21)

Aldehydes from acid Chlorides by Reduction of Ester–mesylates with Sodium Borohydride: Cyclobutanecarboxaldehyde (51, 11)

Cyclic Ketones from 1,3–Dithiane: Cyclobutanone (51, 76)

Cyclobutanone from Methylenecyclopropane via Oxaspiropentane (57, 36)

Cyclobutanone Via Solvolytic Cyclization (54, 84)

One–carbon Ring Expansion of Cycloalkanones to Conjugated Cycloalkenones: 2–Cyclohepten–1–one (59, 113)

Nitriles from Ketones: Cyclohexanecarbonitrile (58, 101)

Aldehydes from Olefins: Cyclohexanecarboxaldehyde (57, 11)

Catalytic Osmium Tetroxide Oxidation of Olefins: cis–1,2–Cyclohexanediol (58, 43)

Stereoselective Hydroxylation with Thallium(i) Acetate and Iodine: trans– and cis–1,2–Cyclohexanediols (59, 169)

Cleavage of Methyl Ethers with Iodotrimethylsilane: Cyclohexanol from Cyclohexyl Methyl Ether (59, 35)

Preparation of , –Unsaturated Aldehydes via the Wittig Reaction: Cyclohexylideneacetaldehyde (53, 104)

Cyclopropenone (57, 41)

Cyclopropyldiphenylsulfonium Tetrafluoroborate (54, 27)

Ring Contraction via a Favorskii–Type Rearrangement: Cycloundecanone (56, 107)

Hydrogenation of Aromatic Nuclei: 1–Decalol (51, 103)

Oxidation with the Chromium Trioxide–Pyridine Complex Prepared in situ: 1–Decanal (55, 84)

Reduction of Alkyl Halides and Tosylates with Sodium Cyanoborohydride in Hexamethylphosphoric Triamide (HMPA): A. 1–Iododecane to n–Decane B. 1–Dodecyl Tosylate to n–Dodecane (53, 107)

Diamantane: Pentacyclo[7.3.1.1^4,12.0^2,7.0^6,11]tetradecane (53, 30)

Macrocyclic Diimines: 1,10–dlazacyclöCtadecane (54, 88)

Dlazoacetophenone (53, 35)

2–diazocycloalkanones: 2–diazocyclohexanone (51, 86)

2–diazopropane (50, 27)

Macrocyclic Polyethers: Dibenzo–18–crown–6 Polyether and Dicyclohexyl–18–crown–6 Polyether (52, 66)

1,2–Diaroylcyclopropanes: trans–1,2–Dibenzoylcyclopropane (52, 33)

,???–Dibromodibenzyl Sulfone (50, 31)

Phosphine–Nickel Complex Catalyzed Cross–Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2–Dibutylbenzene (58, 127)

Oxidation with Bis(Salicylidene)ethylenediiminocobalt(II) (Salcomine); 2,6–Di–tert–butyl–p–benzoquinone (57, 78)

Diazo Transfer by Means of Phase–transfer Catalysis: Di–tert–Butyl Diazomalonate (59, 66)

Di–tert–butyl Dicarbonate (57, 45)

cis–3,4–Dichlorocyclobutene (50, 36)

cis–Dichloroalkanes from Epoxides: cis–1,2–Dichlorocyclohexane (58, 64)

2,3–Dicyanobutadiene as a Reactive Intermediate by in situ Generation from 1,2–Dicyanocyclobutene: 2,3–Dicyano–1,4,4a,9a–tetrahydrofluorene (58, 67)

Dideuteriodiazomethane (53, 38)

Diethylaluminum cyanide (52, 90)

Diethylaminosulfur trifluoride (57, 50)

Diethyl tert–Butylmalonate (50, 38)

2–Trimethylsilyloxy–1,3–butadiene as a Reactive Diene: Diethyl trans–4–Trimethylsilyloxy–4–cyclohexene–1,2–dicarboxylate (58, 163)

Diethyl 2–(Cyclohexylamino)vinylphosphonate (53, 44)

Radical Anion Arylation: Diethyl Phenylphosphonate (58, 134)

Diethyl trans– ⁴–Tetrahydrophthalate (50, 43)

Homogeneous Catalytic Hydrogenation: Dihydrocarvone (53, 63)

trans–1,2–Dihydrophthalic Acid (50, 50)

5,6–Dihydro–2H–pyran–2–one and 2H–Pyran–2–One (56, 49)

2,4–Dimethoxybenzonitrile (50, 52)

Biaryls from Simple Arenes via Organotellurium Intermediates; 4,4’–Dimethoxy–1,1’–Biphenyl (57, 18)

6,7–Dimethoxy–3–Isochromanone (55, 45)

Regioselective Mannich Condensation with Dimethyl(methylene)ammonium Trifluoroacetate: 1–Dimethylamino–4–methyl–3–pentanone (59, 153)

Directed Lithiation of Aromatic Compounds: (2–Dimethylamino–5–methylphenyl)diphenylcarbinol (53, 56)

Use of Dipotassium Nitrosodisulfonate (fremy’s Salt): 4,5–Dimethyl–o–Benzoquinone (52, 88)

1,2–Dimethylcyclobutenes by Reductive Ring–Contraction of Sulfolanes: cis–7,8–Dimethylbicyclo[4.2.0]oct–7–Ene (57, 53)

4,4’–Dimethyl–1,1’–biphenyl (55, 48)

N,N–Dimethyl–5 –cholest–3–Ene–5–acetamide (54, 77)

Conversion of Esters to Amides with Dimethylaluminum Amides: N,N–Dimethylcyclohexanecarboxamide (59, 49)

4,4–Dimethyl–2–Cyclohexen–1–one (53, 48)

Reductive Amination with Sodium Cyanoborohydride: N,N– Dimethylcyclohexylamine (52, 124)

N,N–Dimethyldodecylamine Oxide (50, 56)

Dimethyl Nitrosuccinate (57, 60)

Dimethyl 2,3–Pentadienedioate (57, 62)

Allylically Transposed Amines from Allylic Alcohols; 3,7–Dimethyl–1,6–octadien–3–amine (58, 4)

Bicyclic Ketones for The Synthesis of Tropinoids: 2 ,4 –Dimethyl–8–oxabicyclo[3.2.1]oct–6–en–3–one (58, 17)

2,2–Dimethyl–4–Phenylbutyric Acid (50, 58)

Cyclopentenones from , ’–Dibromoketones and Enamines: 2,5–Dimethyl–3–phenyl–2–cyclopenten–1–one (58, 56)

Alkylations of Aldehydes via Reaction of the Magnesioenamine Salt of an Aldehyde: 2,2–Dimethyl–3–phenylpropionaldehyde (54, 46)

3,5–Dinitrobenzaldehyde (53, 52)

2,3–Diphenyl–1,3–butadiene (50, 62)

Reagents for Synthesis of Organoselenium Compounds: Diphenyl Diselenide and Benzeneselenenyl Chloride (59, 141)

Aromatic Hydrocarbons from Aromatic Ketones and Aldehydes: 1,1–Diphenylethane (55, 7)

Nucleophilic –sec–Aminoalkylation: 2–(Diphenylhydroxymethyl)pyrrolidine (58, 113)

Diphenylketene (52, 36)

Alkenes via Hofmann Elimination: Use of Ion–Exchange Resin for Preparation of Quaternary Ammonium Hydroxides: Diphenylmethyl Vinyl Ether (55, 3)

2,3–Diphenylvinylene Sulfone (50, 65)

1,3–Dithiane (50, 72)

2,2’–Dithienyl Sulfide (50, 75)

Selective Epoxidation of Terminal Double Bonds: 10, 11–Epoxyfarnesyl Acetate (56, 112)

1–Ethoxy–1–butyne (57, 65)

Demethylation of Methyl Aryl Ethers: 4–Ethoxy–3–hydroxybenzaldehyde (56, 44)

Carbine Generation by –Elimination with Lithium 2,2,6,6–Tetramethylpiperidide: 1–Ethoxy–2–p–tolylcyclopropane (58, 37)

Esterification of Carboxylic Acids with Trialkyloxonium Salts; Ethyl and Methyl 4–Acetoxybenzoates (56, 59)

ortho–Alkylation of Anilines: Ethyl 4–Amino–3–Methylbenzoate (56, 15)

Ethyl 5 –Cholest–3–ene–5–acetate (54, 74)

Free–Radical Cyclization: Ethyl 1–Cyano–2–Methylcyclohexanecarboxylate (55, 57)

2,2–(Ethylenedithio)cyclohexanone (54, 37)

A General Synthesis of 4–Isoxazolecarboxylic Esters: Ethyl 3–Ethyl–5–methyl–4–isoxazolecarboxylate (53, 59)

3–Alkyl–1–alkynes Synthesis: 3–Ethyl–1–hexyne (58, 1)

–Hydroxy Esters from Ethyl Acetate and Aldehydes or Ketones: Ethyl 1–Hydroxycyclohexylacetate (53, 66)

Indoles from Anilines: Ethyl 2–Methylindole–5–carboxylate (56, 72)

Stereoselective Synthesis of Trisubstituted Olefins: Ethyl 4–Methyl–(E)–4,8–nonadienoate (53, 116)

Metalation of 2–Methylpyridine Derivatives: Ethyl 6–Methylpyridine–2–acetate (52, 75)

Ethyl 1–Naphthylacetate (50, 77)

Ethyl (E)–3–Nitroacrylate [Replaced by Methyl (E)–3–Nitroacrylate] (56, 65; replaced)

–Ketoesters from Aldehydes via Diethyl Acylsuccinates: Ethyl 4–oxohexanoate (58, 79)

Ethyl Pyrrole–2–Carboxylate (51, 100)

Thiazoles from Ethyl Isocyanoacetate and Thiono Esters: Ethyl Thiazole–4–carboxylate (59, 183)

Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid (56, 28)

Fluorinations with Pyridinium Polyhydrogen Fluoride Reagent: 1–Fluoroadamantane (58, 75)

Aldehydes from Aromatic Nitriles: 4–Formylbenzenesulfonamide (51, 20)

Geranyl Chloride (54, 63)

Allylic Chlorides from Allylic Alcohols: Geranyl Chloride (54, 68)

Glutaconaldehyde Sodium Salt From Hydrolysis of Pyridinium–1–sulfonate (59, 79)

Aldehydes from Primary Alcohols by Oxidation with Chromium Trioxide: Heptanal (52, 5)

Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5–Heptanedione (56, 36)

Macrocyclic Polyamines: 1,4,7,10,13,16–Hexaäzacycloöctadecane (58, 86)

Cuprous Ion–Catalyzed Oxidative Cleavage of Aromatic o–Diamines by Oxygen:(Z,Z)–2,4–Hexadienedinitrile (57, 33)

Hexafluoroacetone Imine (50, 81)

3–Trimethylsilyl–3–buten–2–one as Michael Acceptor for Conjugate Addition–Annelation: cis–4,4a,5,6,7,8–Hexahydro–4a,5–dimethyl–2(3H)–naphthalenone (58, 158)

Nitrones for Intramolecular 1,3–Dipolar Cycloadditions: Hexahydro–1,3,3,6–tetramethyl–2,1–benzisoxazoline (58, 106)

(E)–4–Hexen–1–ol (55, 62)

Fragmentation of , –Epoxyketones to Acetylenic Aldehydes and Ketones: Preparation of 2,3–Epoxycyclohexanone and its Fragmentation to 5–Hexynal (55, 52)

–Hydroxy– , –Unsaturated Aldehydes via 1,3–Bis(methylthio)allyllithium: trans–4–Hydroxy–2–hexenal (54, 19)

17 –Hydroxy–5–oxo–3,5–seco–4–norandrostane–3–carboxylic Acid (55, 67)

Directed Aldol Condensations: threo–4–Hydroxy–3–phenyl–2–heptanone (54, 49)

Macrolides from Cyclization of –Bromocarboxylic Acids: 11–Hydroxyundecanoic Lactone (58, 98)

Direct Iodination of Polyalkylbenzenes: Iododurene (51, 94)

trans–Iodopropenylation of Alkyl Halides: (E)–1–Iodo–4–phenyl–2–butene (56, 77)

2–Iodo–p–xylene (55, 70)

cis– , –Unsaturated Acids: Isocrotonic Acid (53, 123)

Trichloromethyl Chloroformate as a Phosgene Equivalent: 3–Isocyanatopropanoyl Chloride (59, 195)

Hydroboration of Olefins: (+)–Isopinocampheol [Replaced by ( )–Isopinocampheol] (52, 59)

( )–Isopinocampheol (New)

Reaction of Aryl Halides with –Allylnickel Halides: Methallylbenzene (52, 115)

Sulfonyl Cyanides: Methanesulfonyl Cyanide (57, 88)

1,6–Methano[10]annulene (54, 11)

Vinyl Sulfides from Thioacetals with Copper(I) Trifluoromethanesulfonate: (Z)–2–Methoxy–1–phenylthio–1,3–butadiene (59, 202)

6–Methoxy– –tetralone (51, 109)

Methyl Groups by Reduction of Aromatic Carboxylic Acids with Trichlorosilane–tri–n–propylamine: 2–Methylbiphenyl (56, 83)

1–d–Aldehydes from Organometallic Reagents: 2–Methylbutanal–1–d (51, 31)

Preparation of Vinyl Trifluoromethanesulfonates: 3–methyl–2–buten–2–yl Triflate (54, 79)

Preparation and Reductive Cleavage of Enol Phosphates: 5–Methylcoprost–3–Ene (52, 109)

Oxymercuration–Reduction: Alcohols from Olefins: 1–Methylcyclohexanol (53, 94)

Reductive Cleavage of Allylic Alcohols, Ethers, or Acetates to Olefins: 3–Methylcyclohexene (56, 101)

–Ketoesters to Prepare Cyclic Diketones: 2–Methyl–1,3–cyclopentanedione (58, 83)

Sulfide Contraction via Alkylative Coupling: 3–Methyl–2,4–Heptanedione (55, 127)

Isoxazole Annelation Reaction: 1–Methyl–4,4a,5,6,7,8–Hexahydronaphthalen–2(3H)–one (53, 70)

Addition of Organolithium Reagents to Allyl Alcohol: 2–Methyl–1–Hexanol (55, 1)

Conversion of Primary Alcohols to Urethanes via the Inner Salt of Methyl (carboxysulfamoyl)Triethylammonium Hydroxide: Methyl n–Hexylcarbamate (56, 40)

Methyl 2–Alkynoates from 3–Alkyl–2–pyrazolin–5–ones: Methyl 2–Hexynoate (55, 73)

Methyl (trans–2–Iodo–1–Tetralin)carbamate (51, 112)

Methyl Nitroacetate (55, 77)

Methyl (E)–3–Nitroacrylate (New)

2–Methyl–2–nitrosopropane and Its Dimer (52, 77)

Nucleophilic Acylation with Disodium Tetracarbonylferrate: Methyl 7–Oxoheptanoate and Methyl 7–Oxoöctanoate (59, 102)

Aldehydes from Allylic Alcohols and Phenylpalladium Acetate: 2–Methyl–3–phenylpropionalde (51, 17)

Endocyclic Enamine Synthesis: N–Methyl–2–phenyl– ²–tetrahydropyridine (54, 93)

Hydrogenolysis of Carbon–Halogen Bonds with Chromium(II)–en Perchlorate: Naphthalene from 1–Bromonaphthalene (52, 62)

Thiophenols from Phenols: 2–Naphthalenethiol (51, 139)

S(–)– –(1–Naphthyl)ethylamine (55, 80)

Alkyl Iodides: Neopentyl Iodide and Iodocyclohexane (51, 44)

Sulfide Synthesis in Preparation of Dialkyl and Alkyl Aryl Sulfides: Neopentyl Phenyl Sulfide (58, 143)

4–Nitrobenzyl Fluoride (57, 72)

1–Nitrocycloöctene (50, 84)

Formation and Photochemical Wolff Rearrangement of Cyclic –Diazo Ketones: D–Norandrost–5–en–3 –ol–16–carboxylic Acids (52, 53)

Highly Reactive Magnesium for the Preparation of Griignard Reagents: 1–Norbornanecarboxylic Acid (59, 85)

^9,10–Octalin (50, 88)

2,2,7,7,12,12,17,17–Octamethyl–21,22,23,24–tetraoxaperhydroquaterene (57, 74)

Orcinol Monomethyl Ether (53, 90)

1,6–Oxido[10]annulene (55, 86)

Cyanide–Catalyzed Conjugate Addition of Aryl Aldehydes: 4–Oxo–4–(3–pyridyl)butyronitrile (59, 53)

Aldehydes from sym–Trithlane: n–Pentadecanal (51, 39)

(Pentafluorophenyl)acetonitrile (57, 80)

Pentafluorophenylcopper Tetramer, a Reagent for Synthesis of Fluorinated Aromatic Compounds (59, 122)

trans–3–Penten–2–one (51, 115)

Arene Oxide Synthesis: Phenanthrene–9,10–oxide (58, 12)

Free–Radical Alkylation of Quinones: 2–Phenoxymethyl–1,4–Benzoquinone (56, 68)

3–Phenyl–2H–azirine–2–carboxaldehyde (57, 83)

Phase–Transfer Alkylation of Nitriles: 2–Phenylbutyronitrile (55, 91)

Directed Aldol Condensations: – Phenylcinnamaldehyde (50, 66)

Aldehydes from 2–Benzyl–4,4,6–Trimethyl–5,6–dihydro–1,3(4H)–oxazine: 1–Phenylcyclopentanecarboxaldehyde (51, 24)

Amines from Mixed Carboxylic–Carbonic Anhydrides: 1–Phenylcyclopentylamine (51, 48)

cis–2–Phenylcyclofropanecarboxylic Acid (50, 94)

Substitution of Aryl Halides with Copper(i) Acetylides: 2–Phenylfuro[3,2–b]pyridine (52, 128)

Ketones and Alcohols from Organoboranes: Phenyl Heptyl Ketone, 1–Hexanol, and 1–Octanol (53, 77)

1–Phenyl–1,4–pentadiyne and 1–Phenyl–1,3–pentadiyne (50, 97)

Phenylation with Diphenyliodonium Chloride; 1–Phenyl–2,4–pentanedione (51, 128)

1–Phenyl–4–phosphorinanone (53, 98)

4–Phenyl–1,2,4–triazoline–3,5–dione (51, 121)

2–Phenyl–2–vinylbutyronitrile (55, 99)

Boranes in Functionalization of Olefins to Amines: 3–Pinanamine (58, 32)

Allylic Oxidation with Hydrogen Peroxide–Selenium Dioxide: trans–Pinocarveol (56, 25)

Base–Induced Rearrangement of Epoxides to Allylic Alcohols: trans–Pinocarveol (53, 17)

Polymeric Carbodiimide. Preparation (56, 95)

Alkynes via Phase Transfer Catalyzed Dehydrohalogenation: Propiolaldehyde Diethyl Acetal (59, 10)

Rearrangement of Bridgehead Alcohols to Polycyclic Ketones by Fragmentation–Cyclization: 4–Protoadamantanone (Tricyclo[4.3.1.0^3.8]Decan–4–One) (59, 147)

Quadricyclane (51, 133)

1,2,3,4–Tetrahydro– –Carboline (51, 136)

Aziridines from –Iodocarbamates: 1,2,3,4–Tetrahydronaphthalene(1,2)Imine (51, 53)

2,3,4,5–Tetrahydropyridine Trimer (56, 118)

3,3,6,6–Tetramethoxy–1,4–Cyclohexadiene (57, 92)

2,2,3,3–Tetramethyliodocyclopropane (52, 132)

4H–1,4–Thiazine l,1–Dioxide (52, 135)

2–Thiophenethiol (50, 104)

p–Tolylsulfonyldiazomethane (57, 95)

p–Tolylsulfonylmethyl Isocyanide (57, 102)

Tri–tert–Butylcyclopropenyl Tetrafluoroborate (54, 97)

Tricarbonyl[2,3,4,5– )–2,4,–Cyclohexadien–1–One]Iron and Tricarbonyl[(1,2,3,4,5– )–2–Methyoxy–2,4–Cyclohexadien–1–Yl]Iron(1+) Hexafluorophosphate(1 ) from Anisole (57, 107)

Alkylation of Dimedone with a Tricarbonyl(diene)Iron Complex: Tricarbonyl[2–[2,3,4,5– )–4–Methoxy–2,4–Cyclohexadien–1–yl]–5,5–Dimethyl–1,3–Cyclohexanedione]iron (57, 16)

Cyclobutadiene in Synthesis: endo–Tricyclo[4.4.0.0^2,5]Deca–3,8–Diene–7,10–Dione (55, 43)

Trifluoroacetylation of Amines and Amino Acids Under Neutral, Mild Conditions: N–Trifluoroacetanilide and N–Trifluoroacetyl–L–Tyrosine (56, 122)

Aldehydes from Acid Chlorides by Modified Rosenmund Reduction: 3,4,5–Trimethoxybenzaldehyde (51, 8)

Oxidation with the Nitrosodisulfonate Radical. I. Preparation and Use of Disodium Nitrosodisulfonate: Trimethyl–p–Benzoquinone (52, 83)

2,2–(Trimethylenedithio)Cyclohexanone (54, 39)

Trimethylene Dithiotosylate and Ethylene Dithiotosylate (54, 33)

Trimethyloxonium Tetrafluoroborate (51, 142)

3,5,5–Trimethyl–2–(2–Oxopropyl)–2–Cyclohexen–1–One (57, 113)

Aldehydes by Oxidation of Terminal Olefins with Chromyl Chloride: 2,4,4–Trimethylpentanal (51, 4)

Trimethylsilyl Azide (50, 107)

3–Trimethylsilyl–3–Buten–2–One: a Michael Acceptor (58, 152)

Tropolone (57, 117)

Preparation of Alkenes by Reaction of Lithium Dipropenylcuprates with Alkyl Halides: (E)–2–Undecene (55, 103; deleted)

General Index

Frmula Index

Hazard Index

Author Index

Concordance Index