The Journal of Organic Chemistry: Volume 28, Issue 6 (ACS Publications)

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June 1963

Volume 28, Issue 6

Pages 1445-1732

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Articles

The Alkaloids of Hunteria eburnea Pichon. II. The Quaternary Bases

M. F. Bartlett, B. Korzun, R. Sklar, A. F. Smith, W. I. Taylor

pp 1445–1449

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a001

First Page

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Reactions of Metal Chelates. V.^1,2 Substitution of Metal Acetylacetonates with Friedel-Crafts Acylating Reagents and Sulfur Electrophiles

James P. Collman, Roger L. Marshall, William L. Young III, Curtis T. Sears Jr.

pp 1449–1455

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a002

First Page

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The Mechanism of the Prins Reaction. III. The Acetolysis of Arenesulfonates of anti-3-Oxabicyclo[3.3.1]nonan-9-ol and trans-6-Hydroxy-cis-3-oxabicyclo[4.3.0]nonane¹

Lloyd J. Dolby, Maurice J. Schwarz

pp 1456–1458

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a003

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The Reaction of Enamines of Cyclic Ketones with Dimethyl Acetylenedicarboxylate¹

Glenn A. Berchtold, George F. Uhlig

pp 1459–1462

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a004

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Enamine Chemistry. I. Reactions with Nonactivated Terminal Acetylenic Compounds¹

Kent C. Brannock, Robert D. Burpitt, John G. Thweatt

pp 1462–1464

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a005

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Enamine Chemistry. II. Reactions with Acetylenedicarboxylates¹

Kent C. Brannock, Robert D. Burpitt, V. Wilson Goodlett, John G. Thweatt

pp 1464–1468

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a006

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Ketenes I. Cycloaddition of Ketene and Dialkylketenes to Enamines

Robert H. Hasek, James C. Martin

pp 1468–1474

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a007

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An Unusual Fragmentation—Rearrangement under Acyloin Reaction Conditions^1,2e

Jordan J. Bloomfield, Robert G. Todd, Lloyd T. Takahashi

pp 1474–1476

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a008

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Elimination Reactions of α-Halogenated Ketones. XI.^1a Kinetic and Product Studies of Amine-Promoted Elimination from 2-Bromo-2-benzyl-4,4-dimethyl-1-tetralone in Benzene

Dennis N. Kevill, Peter W. Foster, Norman H. Cromwell

pp 1476–1479

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a009

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Comparison of 9-Phenylfluorenyl and Triphenylmethyl in the Decomposition of Azo Compounds^1a,b

Saul G. Cohen, Fredric Cohen, Chi-Hua Wang

pp 1479–1484

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a010

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Some Reactions of Diazomethane with Carbon Dioxide and Ammonia in Aqueous Solution

G. A. Akoyunoglou, Melvin Calvin

pp 1484–1487

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a011

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Syntheses of 1,3-Diazaphenothiazines.¹ I.

Arthur P. Phillips, Nariman B. Mehta, Justina Zupicich Strelitz

pp 1488–1490

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a012

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Thiadiazoles. II. Formation of 4-Amino-1,2,5-thiadiazole-3-carboxylic Acid and Its Derivatives by Ring-Cleavage of [1,2,5]Thiadiazolo[3,4-d]pyrimidin-7(6H)-one^1,2

Y. Fulmer Shealy, Joe D. Clayton

pp 1491–1495

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a013

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Preparation and Reactions of 1-(Nitroguanyl)aziridines

James U. Lowe Jr., Takahiko A. Oda, Robert Evans

pp 1496–1498

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a014

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Small Charged Rings. III. Heterocyclic Ring Expansion through Aziridinium Salts^1-3

Nelson J. Leonard, Klaus Jann, Joseph V. Paukstelis, C. K. Steinhardt

pp 1499–1506

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a015

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Polynucleotides. I. Synthesis of Uridylyl-(3' → 5')-uridine and Uridylyl-(3' → 5')-6-azauridine

Ross H. Hall, Roosevelt Thedford

pp 1506–1509

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a016

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Pteridine Chemistry. X. Methylation Studies. III. Steric Effects of Phenyl Groups at C-6 and C-7¹

Robert B. Angier

pp 1509–1513

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a017

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The Darzens Condensation. II. Reaction of Chloroacetamides with Aromatic Aldehydes

C. C. Tung, A. J. Speziale, H. W. Frazier

pp 1514–1521

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a018

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Reaction of Amides and Esters of α,β-Dibromopropionic Acids with Triphenylphosphine

C. C. Tung, A. J. Speziale

pp 1521–1523

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a019

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The Preparation of 14β,21-Epoxy Steroids

Milton Heller, Francis J. McEvoy, Seymour Bernstein

pp 1523–1527

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a020

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C-3 Substituted ¹⁽¹⁰⁾-Steroids^1,2

Jack Fishman

pp 1528–1530

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a021

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A Stereospecific Synthesis of C-21-Methylated Corticosteroids^1a,d

E. J. Agnello, S. K. Figdor, G. M. K. Hughes, H. W. Ordway, Rex Pinson Jr., B. M. Bloom, G. D. Laubach

pp 1531–1539

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a022

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Proton Magentic Resonance and Stereochemistry of 1-Ethynyl-2-tolylcyclohexanols¹

Alain C. Huitric, William S. Stavropoulos, Bernard J. Nist

pp 1539–1542

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a023

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4-(p-Tolyl)-1-pentanol in Douglas Fir Pulping Products¹

Elliot N. Marvell, Robert Wiman

pp 1542–1545

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a024

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The meso and Racemic Forms of 2,4-Pentanediol and Certain of Their Derivatives

J. G. Pritchard, R. L. Vollmer

pp 1545–1549

Publication Date: June 1963 (Article)

DOI: 10.1021/jo01041a025

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The Acetylation of Some Substituted Ferrocenes¹

David W. Hall, John H. Richards

pp 1549–1554

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a026

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Base Strengths of Alkylpyridines Using Triethylaluminum as the Reference Acid. A Study in F Strain

Donald F. Hoeg, Samuel Liebman, Leo Schubert

pp 1554–1557

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a027

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Lethargic Reactions. I. The Preparation of Hindered Oximes

D. E. Pearson, O. D. Keaton

pp 1557–1558

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a028

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An Arabinoglucoglycan in Chick-Pea Seed

A. R. S. El-Hanafy, Mahmoud I. Taha

pp 1559–1561

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a029

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An Investigation of the Hydrolysis of a Reduced 4-O-Methylglucuronoxylan¹

Samuel C. McKee, E. E. Dickey

pp 1561–1563

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a030

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The Synthesis of a Glucosaminyl-Muramic Acid Disaccharide: Methyl 6-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-acetamido-4-O-acetyl-2-deoxy-3-O-[D-1-(methyl carboxylate)ethyl]-α-D-glucopyranoside¹

Harold M. Flowers, Roger W. Jeanloz

pp 1564–1567

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a031

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Derivatives of 6-Deoxy-6-mercapto-D-fructose¹

M. S. Feather, Roy L. Whistler

pp 1567–1569

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a032

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Thioglycosides of 3-Amino-3-deoxy-D-mannose¹

M. L. Wolfrom, D. Horton, H. G. Garg

pp 1569–1572

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a033

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C-19 Functional Steroids. V.¹ Synthesis of Estrogen Biosynthesis Intermediates²

Timothy Jen, Manfred E. Wolff

pp 1573–1575

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a034

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Solvent Effects in the Menschutkin Reaction

John D. Reinheimer, John D. Harley, Wayne W. Meyers

pp 1575–1579

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a035

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Addition Reactions Induced by Ionizing Radiation. I. Bromotrichloromethane to Butadiene

Catherine S. Hsia Chen, Robert F. Stamm

pp 1580–1585

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a036

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Addition Reactions Induced by Ionizing Radiation. II. Bromotrichloromethane to Isoprene and 2,3-Dimethylbutadiene

Catherine S. Hsia Chen, Evalyn F. Hosterman

pp 1585–1589

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a037

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Potential Radiation-Protective Compounds. Synthesis of the Three Isomeric Three-Carbon Aminohydroxy Bunte Salts and Related Compounds¹

D. H. Ball, J. M. Williams, L. Long Jr.

pp 1589–1593

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a038

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Electronic Effects on the Stereochemistry of the Diels—Alder Reaction¹

Fred Kaplan, Harold Conroy

pp 1593–1596

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a039

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Reactions of Ethylene Diisothiocyanate with Primary and Secondary Amines¹

F. D'Angeli, A. Bandel, V. Giormani

pp 1596–1600

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a040

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Interaction of Phenyl Isocyanate and Related Compounds with Sodium Borohydride¹

S. E. Ellzey Jr., Charles H. Mack

pp 1600–1604

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a041

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S-[ι-(Aminoöxy)alkyl]isothiuronium Salts, ι,ι'-Bis(aminoöxy)alkanes and Related Compounds¹

Ludwig Bauer, K. S. Suresh

pp 1604–1608

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a042

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Some Chemical Reactions of 3,9-Dichloro-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane 3,9-Dioxide

Rudi Rätz, Orville J. Sweeting

pp 1608–1612

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a043

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Reaction of 3,9-Dichloro-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane 3,9-Dioxide with Dimethyl Sulfoxide

Rudi Rätz, Orville J. Sweeting

pp 1612–1616

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a044

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The Dehydrobromination of 3-Methoxy-17α-bromoestra-1,3,5(10)-trien-16-one

William F. Johns

pp 1616–1619

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a045

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Acyl Transfer during Chromium Trioxide Oxidation in the Pregnane Series. Some Reactions of 5 β-Androstane-16,17-ketols^1,2

C. H. Kuo, D. Taub, N. L. Wendler

pp 1619–1624

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a046

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Synthesis of 2,2-Diarylpropanes by Hydride Transfer¹

Carl Serres, Ellis K. Fields

pp 1624–1627

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a047

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Polynuclear Aromatic Hydrocarbons. XI.¹ The Synthesis of Molecularly Overcrowded Benzo(c)phenanthrenes. I

Donald D. Phillips, Michael F. Bruno

pp 1627–1632

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a048

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Optical Rotatory Dispersion Studies. LXXXII.^1a Conformational Analysis. XXXVII.^1b Determination of the Stereochemistry and Conformation of the Four Isomeric Cyanodihydrocarvones by Optical Rotatory Dispersion and Dipole Moment Measurements²

Carl Djerassi, R. A. Schneider, H. Vorbrueggen, N. L. Allinger

pp 1632–1638

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a049

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The Constitution of Otobain

N. S. Bhacca, Robert Stevenson

pp 1638–1642

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a050

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Chemistry of Carbon Diselenide. I. Reactions with Primary Amines¹

J. S. Warner

pp 1642–1644

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a051

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The Claisen Rearrangement of Allyl Ethers of α-Hydroxybenzalacetophenones¹

R. Percy Barnes, Francis E. Chigbo

pp 1644–1646

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a052

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Structures of Substituted Fulvenes. The Reaction Products from Acetone and Dimethylfulvene

Donald M. Fenton, Marvin J. Hurwitz

pp 1646–1651

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a053

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The Preparation of Dodecamethylcyclohexasilane

Henry Gilman, Richard A. Tomasi

pp 1651–1653

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a054

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Intramolecular Reactions of Some Cyclic β-Diketones¹

Howard J. Schaeffer, Robert Vince

pp 1653–1656

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a055

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Furazan Oxides. III. An Unusual Type of Aromatic Substitution Reaction^1,2

Frank B. Mallory, Suzanne P. Varimbi

pp 1656–1662

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a056

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Electron Density and Orientation of Nucleophilic Substitution in the Purine Ring¹

Edward Y. Sutcliffe, Roland K. Robins

pp 1662–1666

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a057

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Aromatic Fluorine Compounds. XI. Replacement of Chlorine by Fluorine in Halopyridines

G. C. Finger, Laurence D. Starr, D. R. Dickerson, H. S. Gutowsky, Jan Hamer

pp 1666–1668

Publication Date: June 1963 (Article)

DOI: 10.1021/jo01041a058

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Aromatic Cyclodehydration. LIII.¹ 6a-Azonianaphthacenequinones

Charles K. Bradsher, Marvin W. Barker

pp 1669–1671

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a059

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The Reaction of 3-Acyl-4-hydroxycoumarins with Ammonium Salts¹

Robert A. Kloss, Charles Wiener

pp 1671–1673

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a060

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1,2-Dicarbonyl Derivatives Resulting from the Action of Nitrosyl Chloride on Alcohols

David T. Manning, Harry A. Stansbury Jr.

pp 1673–1675

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a061

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Effect of Remotely Positioned Groups on the Reactivities of Olefins toward Radical Addition¹

Earl S. Huyser, J. Dale Taliaferro

pp 1676–1678

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a062

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Isomerization and Disproportionation of d-Limonene on Silica Gel

G. L. K. Hunter, William B. Brogden Jr.

pp 1679–1682

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a063

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Pyrazines. III. The Action of Phosphoroyl Chloride on Pyrazine N-Oxides^1,2

B. Klein, N. E. Hetman, M. E. O'Donnell

pp 1682–1686

Publication Date: June 1963 (Article)

DOI: 10.1021/jo01041a064

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Carbonium Ion Intermediates in the Deamination of 3-Methyl-2-butylamine and Isopentylamine¹

Marc S. Silver

pp 1686–1690

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a065

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The Isolation of a Second Octulose and of a Heptose from the Avocado: D-glycero-L-galacto-Octulose and D-glycero-D-galacto-Heptose¹

Hugo H. Sephton, Nelson K. Richtmyer

pp 1691–1694

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a066

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Hydride Ion Abstraction with Antimony Pentachloride

J. Holmes, R. Pettit

pp 1695–1696

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a067

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Enamine Chemistry. III. The Reaction of Ketene Acetals, O,N-Acetals, and N,N-Acetals with Acetylenic Esters

Kent C. Brannock, Robert D. Burpitt, John G. Thweatt

pp 1697–1698

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a501

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Determination of the Configuration of C-9 in Levopimaric Acid¹

William G. Dauben, Robert M. Coates

pp 1698–1699

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a502

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β-Bromocrotonolactone from the Bromination of Furoic Acid

Tom J. Mabry

pp 1699–1700

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a503

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Triethylsilyltriethylgermane¹

James M. Shackelford, Hannibal De Schmertzing, Charles H. Heuther, Harold Podall

pp 1700–1702

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a504

First Page

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Chlorination of 2,3-Dimethylpyrazine

Robert A. Pages, Paul E. Spoerri

pp 1702–1703

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a505

First Page

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The Cleavage of Aryl Ethers by Alkali Metals in Aliphatic Ether Solvents. Detection by Electron Spin Resonance¹

Dolan H. Eargle Jr.

pp 1703–1705

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a506

First Page

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The Conversion of 2-Acetoxypulegone to Menthofuran. Terpenes. V.¹

L. H. Zalkow, J. W. Ellis, Sister M. Roger Brennan

pp 1705–1707

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a507

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Reductions with Triphenyltin Hydride

Donald H. Lorenz, Ernest I. Becker

pp 1707–1708

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a508

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Multi-nuclear Ferrocenes. I. Biferrocenyl^1a,b

Stanley I. Goldberg, Dana W. Mayo, John A. Alford

pp 1708–1710

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a509

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Preparation of Bicyclo[4.3.1]dec-7-en-10-one

Richard D. Sands

pp 1710–1712

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a510

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Cyanoethylation of Butadiene Sulfone

Richard P. Welcher

pp 1712–1713

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a511

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The Chloromethylation of 5-Nitrosalicylaldehyde

Lloyd D. Taylor, Robert B. Davis

p 1713

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a512

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The Preparation of 1-Aryl-1,2-cyclopropanedicarboximides. An Application of Dimethylsulfoxonium Methylide

Patrick T. Izzo

pp 1713–1715

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a513

First Page

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A Convenient Synthesis of 1,2,5,6-Dibenzocyclooctatetraene¹

C. E. Griffin, Joan A. Peters

pp 1715–1716

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a514

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Synthesis of 7-Methyl- and 7-Phenylnorbornadiene

Paul R. Story, Susan R. Fahrenholtz

pp 1716–1717

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a515

First Page

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Fluorine-Containing Nitrogen Compounds. V. Difluoronitroacetamidines and Difluoronitromethyl-1,2,4-triazoles^1,2

Eugene R. Bissell

pp 1717–1720

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a516

First Page

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Addition Compounds of Thiols and 1-Substituted Nicotinamides^1,2

D. C. Dittmer, J. M. Kolyer

pp 1720–1722

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a517

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The Conjugate 1:4-Addition of Some Acetylenic Grignard Reagents to Cyclohexylidenemalononitrile

W. Parker, R. Ramage

pp 1722–1724

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a518

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Anomalous Reduction of Malonic Esters with Lithium Aluminum Hydride

William J. Bailey, Matthew E. Hermes, William A. Klein

pp 1724–1725

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a519

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Reactions of Phenyl-Substituted Methanes and Ethanes with Lithium or n-Butyllithium

Henry Gilman, Bernard J. Gaj

pp 1725–1727

Publication Date: June 1963 (Article)

DOI: 10.1021/jo01041a520

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Some Gas-Phase Reactions of Fluoroallyl Halides^1a

Paul Tarrant, John Savory

pp 1728–1730

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a521

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Ring Conformation in Methyl α- and β-D-Xylothiapyranosides as Demonstrated by Nuclear Magnetic Resonance¹

V. S. R. Rao, Joseph F. Foster, Roy L. Whistler

pp 1730–1731

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a522

First Page

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Dipole Moments of Two Nitrogen Analogs of Sesquifulvalene

W. D. Kumler

pp 1731–1732

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a523

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Communication TO THE EDITOR

p 1732

Publication Date: June 1963 ()

DOI: 10.1021/jo01041a069

First Page

Hi-Res PDF[127K]

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