The Journal of Organic Chemistry: Volume 58, Issue 24 (ACS Publications)

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November 1993

Volume 58, Issue 24

Pages 6531-6938

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Articles

Carboranyl oligonucleotides. 1. Synthesis of thymidine(3',5')thymidine (o-carboran-1-ylmethyl)phosphonate

Zbigniew J. Lesnikowski, Raymond F. Schinazi

pp 6531–6534

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a001

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Conformational isomerism of calix[6]arenes: isolation of two conformational isomers of the 1,2-bis(p-tert-butylbenzyl) ether of p-tert-butylcalix[6]arene

Placido Neri, Concetta Rocco, Grazia M. L. Consoli, Mario Piattelli

pp 6535–6537

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a002

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Regioselectivity in forming dipole-stabilized anions. Sites of metalation of indolines, tetrahydroquinolines, and benzazepines activated by N-formimidoyl or N-Boc groups

A. I. Meyers, Guy Milot

pp 6538–6540

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a003

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Samarium diiodide-promoted reductive cleavage of carbon-sulfur bonds: a novel stereoselective generation of functionalized vinylsamarium species and synthesis of .beta.-thiobutenolides

Makoto Hojo, Hajime Harada, Junji Yoshizawa, Akira Hosomi

pp 6541–6542

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a004

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Catalytic asymmetric allylation reactions. 3. Extension to methallylstannane, comparison of procedures, and observation of a nonlinear effect

Gary E. Keck, Dhileepkumar Krishnamurthy, Mark C. Grier

pp 6543–6544

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a005

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High-precision asymmetric synthesis of stegobiol and stegobinone via boronic esters

Donald S. Matteson, Hon Wah Man

pp 6545–6547

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a006

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Resolution of enantiomers of cis- and trans-fused C60-enone [2+2] photoadducts

Stephen R. Wilson, Yunhui Wu, Nikolas A. Kaprinidis, David I. Schuster, Christopher J. Welch

pp 6548–6549

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a007

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Novel rotaxanes based on the inclusion complexation of biphenyl guests by cyclobis(paraquat-p-phenylene)

Emilio Cordova, Richard A. Bissell, Neil Spencer, Peter R. Ashton, J. Fraser Stoddart, Angel E. Kaifer

pp 6550–6552

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a008

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Porous surfactants from cone conformers of calix[5]arenes

Petr Dedek, Vaclav Janout, Steven L. Regen

pp 6553–6555

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a009

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Tandem enediyne-radical cyclization expansion to nonaromatic enediynes

Janet Wisniewski Grissom, Trevor L. Calkins, Heidi A. McMillen

pp 6556–6558

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a010

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Aryl radical additions to aldehydes and oxime ethers: the tandem enediyne-radical cyclization

Janet Wisniewski Grissom, Detlef Klingberg

pp 6559–6564

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a011

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Biogenetically diverse, bioactive constituents of a sponge, order Verongida: bromotyramines and sesquiterpene-shikimate derived metabolites

Mark T. Hamann, Paul J. Scheuer, Michelle Kelly-Borges

pp 6565–6569

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a012

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Ambigol A and B: new biologically active polychlorinated aromatic compounds from the terrestrial blue-green alga Fischerella ambigua

Beatrix S. Falch, Gabriele M. Koenig, Anthony D. Wright, Otto Sticher, Heinz Ruegger, Gerald Bernardinelli

pp 6570–6575

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a013

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Biosynthesis of the phenazine antibiotics, the saphenamycins and esmeraldins, in Streptomyces antibioticus

Clinton W. Van't Land, Ursula Mocek, Heinz G. Floss

pp 6576–6582

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a014

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New compounds of the manumycin group of antibiotics and a facilitated route for their structure elucidation

Isabel Sattler, Christine Groene, Axel Zeeck

pp 6583–6587

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a015

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Chemistry and structure of ganefromycin

Guy T. Carter, Douglas W. Phillipson, Robert R. West, Donald B. Borders

pp 6588–6595

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a016

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Synthesis of philanthotoxin analogs with a branched polyamine moiety

Aristotle G. Kalivretenos, Koji Nakanishi

pp 6596–6608

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a017

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Conformationally defined analogs of prolylamides. trans-Prolyl peptidomimetics

Charles J. Andres, Timothy L. Macdonald, Timothy D. Ocain, Daniel Longhi

pp 6609–6613

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a018

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Palladium-catalyzed coupling of terminal alkynes with 5-(trifluoromethanesulfonyloxy)pyrimidine nucleosides

Geoffrey T. Crisp, Bernard L. Flynn

pp 6614–6619

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a019

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Ring enlargement of diaziridinone with 2-substituted pyrrole leading to bicyclic triazine and its transformation to novel mesomeric betaine

Mitsuo Komatsu, Mitsuharu Kobayashi, Shinobu Itoh, Yoshiki Ohshiro

pp 6620–6624

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a020

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Convenient synthesis of 2-amino-1,8-naphthyridines, building blocks for host-guest and self-assembling systems

Edward E. Fenlon, Thomas J. Murray, Monica H. Baloga, Steven C. Zimmerman

pp 6625–6628

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a021

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Reactions of methyl(2,5,5-trimethyl-l-cyclopenten-l-yl)carbene and the photochemistry of 2-(1-propynyl)-2,5,5-trimethylcyclopentanone

D. Venugopal, Paul Margaretha, William C. Agosta

pp 6629–6633

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a022

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SINDO1 study of the photoreaction of tetramethylene sulfoxide

Karl Jug, Frank Neumann, Hans Peter Schluff

pp 6634–6640

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a023

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Photoinduced electron transfer and subsequent chemical reactions of adsorbed thianthrene on clay surfaces

Yun Mao, J. Kerry Thomas

pp 6641–6649

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a024

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Crown ether-substituted indene and 3,4-dimethylcyclopentadiene

Herbert Plenio, Ralph Diodone

pp 6650–6653

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a025

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Conformational studies of dihydrotetraphenylmethanes. 2. X-ray crystallographic and solution proton NMR studies of cis-1,4-dihydro-4-tritylbiphenyl and its 4'-bromo derivative: conformational control by an intramolecular edge-to-face aromatic interaction

Martin C. Grossel, Anthony K. Cheetham, David A. O. Hope, Simon C. Weston

pp 6654–6661

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a026

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Transmission of internal rotations: correlated, uncorrelated, and localized disrotatory rotations in propeller chains

Ariel B. Lindner, Flavio Grynszpan, Silvio E. Biali

pp 6662–6670

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a027

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Mixed organofluorine-organosilicon chemistry. 3. A highly efficient and convenient synthesis of aryl perfluoroalk-1-enyl ketones from perfluoroalkyl iodides and aroylsilanes

Boniface Dondy, Charles Portella

pp 6671–6674

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a028

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Mixed organofluorine-organosilicon chemistry. 4. Perfluoroenoxysilanes: synthesis and reactivity

Pascale Doussot, Charles Portella

pp 6675–6680

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a029

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Novel macrocycles from metal-catalyzed oxidative cyclizations of a,c-biladiene salts

Paul A. Liddell, Kevin R. Gerzevske, Jack J. Lin, Marilyn M. Olmstead, Kevin M. Smith

pp 6681–6691

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a030

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Receptors for oxo acids: effects of intra-ion-pair hydrogen bonding on acid-base equilibria

Kei Manabe, Kimio Okamura, Tadamasa Date, Kenji Koga

pp 6692–6700

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a031

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Unusual stability of N-methylmaleimide cycloadducts: characterization of isobenzofuran retro-Diels-Alder reactions

David Tobia, Roy Harrison, Brian Phillips, Thomas L. White, Marcello DiMare, Bruce Rickborn

pp 6701–6706

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a032

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Reductive cleavage of N-substituted 2-aryl-1,3-oxazolidines: generation of .alpha.-amino-substituted carbanions

Ugo Azzena, Giovanni Melloni, Cristina Nigra

pp 6707–6711

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a033

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Interesting products derived from the reactions of 2,3-diamino-2,3-dimethylbutane

Janet L. Gagnon, Thomas R. Walters, Walter W. Zajac Jr., John H. Buzby

pp 6712–6715

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a034

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Synthesis of nitrocyclopentanes via a 3+2 strategy

Eugene Ghera, Tamar Yechezkel, Alfred Hassner

pp 6716–6724

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a035

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Synthesis and revised structure of garuganin III

Gyorgy M. Keseru, Zoltan Dienes, Mihaly Nogradi, Maria Kajtar-Peredy

pp 6725–6728

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a036

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Structural features of solid-state calix[4]arene in the cone conformation

Kenny B. Lipkowitz, Greg Pearl

pp 6729–6736

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a037

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Novel photoreductive cyclization of 1-aryl-2-methylpropane-1,3-diones

Michikazu Yoshioka, Nobuko Ishizuka, Akiko Sano, Sanae Kuwabara, Yoshinobu Yokomori, Tadashi Hasegawa

pp 6737–6739

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a038

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Unusual stereoselectivity in the Diels-Alder addition of cyclopentadiene with the bicyclo[2.2.2]octene nucleus

Richard Vaughan Williams, Murali Mohan Reddy Todime, Paul Enemark, Dick van der Helm, Safia Khalil Rizvi

pp 6740–6744

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a039

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Regioselectivity of Diels-Alder reactions of a surfactant 1,3-diene with surfactant dienophiles

David A. Jaeger, Jinkang Wang

pp 6745–6755

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a040

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A selectivity study of activated ketal reduction with borane dimethyl sulfide

Birgit Bartels, Roger Hunter

pp 6756–6765

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a041

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Stereoselective synthesis of 2-amino alcohols by use of an isocyanide as an aminomethylene equivalent

Masahiro Murakami, Hajime Ito, Yoshihiko Ito

pp 6766–6770

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a042

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Formation and structure of stable, isolable conjugated primary enamines

Gerhard Erker, Ronald Pfaff, Dorothee Kowalski, Ernst Ulrich Wuerthwein, Carl Krueger, Richard Goddard

pp 6771–6778

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a043

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Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita

Michael Miller, Louis S. Hegedus

pp 6779–6785

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a044

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Synthesis of 1-phosphaspiro[2.n]alkanes by addition of terminal phosphinidene complexes to exocyclic olefins

Jui Te Hung, Suh Wan Yang, Gary M. Gray, Koop Lammertsma

pp 6786–6790

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a045

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Organoboranes. 57. Relative efficacy of representative lithium dialkylamide bases for the in situ metalation of allyl chloride to produce (.alpha.-chloroallyl)lithium. Application of the reagent to B-alkoxy-9-borabicyclononanes producing new routes to interesting cyclooctane derivatives

Herbert C. Brown, Seetharaman Jayaraman

pp 6791–6794

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a046

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Intramolecular [4 + 3]-cycloadditions of photochemically generated oxyallyl zwitterions: a route to functionalized cyclooctanoid skeletons

F. G. West, Claudia Hartke-Karger, Daniel J. Koch, Cynthia E. Kuehn, A. M. Arif

pp 6795–6803

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a047

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Total syntheses of (+)-hypusine and its (2S,9S)-diastereomer

Raymond J. Bergeron, Michael X. B. Xia, Otto Phanstiel IV

pp 6804–6806

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a048

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Macrolactonization-transannular aldol condensation approach to the taxane AB ring system

Ki Byung Chai, Paul Sampson

pp 6807–6813

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a049

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Concise synthesis of enantiomerically pure cis- and trans-3-(diphenylphosphino)-4-hydroxytetrahydrofurans

Armin Boerner, Jens Holz, Jacques Ward, Henri B. Kagan

pp 6814–6817

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a050

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Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates

Youichi Ishii, Chao Gao, Wen Xiang Xu, Masakazu Iwasaki, Masanobu Hidai

pp 6818–6825

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a051

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Catalytic asymmetric construction of morpholines and piperazines by palladium-catalyzed tandem allylic substitution reactions

Yasuhiro Uozumi, Asako Tanahashi, Tamio Hayashi

pp 6826–6832

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a052

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Metal-halogen exchange-initiated intramolecular conjugate addition reactions of conjugated acetylenic esters

Manning P. Cooke Jr.

pp 6833–6837

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a053

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The invention of radical reactions. Part 32. Radical deoxygenations, dehalogenations, and deaminations with dialkyl phosphites and hypophosphorous acid as hydrogen sources

Derek H. R. Barton, Doo Ok Jang, Joseph C. Jaszberenyi

pp 6838–6842

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a054

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Tetramethyl 1,1,4,4-cyclohexanetetracarboxylate: preparation and conversion to key precursors of fluorinated, stereochemically defined cyclohexanes

Charles R. Davis, Dale C. Swenson, Donald J. Burton

pp 6843–6850

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a055

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Macrocyclization through radical-mediated vinylcyclopropane/alkene condensation. Facile entry into the brefeldin ring system

Ken S. Feldman, Heidi M. Berven, Anthony L. Romanelli, Masood Parvez

pp 6851–6856

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a056

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Formation of trans ring-fused compounds by an alkylation-radical cyclization sequence

Derrick L. J. Clive, Hartford W. Manning, Taryn L. B. Boivin, Maarten H. D. Postema

pp 6857–6873

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a057

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A means for stereocontrolled introduction of the C-2 oxygen substituent in functionalized cis-tricyclo[9.3.1.03,8]pentadecanones related to taxol

Leo A. Paquette, Scot K. Huber, Richard C. Thompson

pp 6874–6882

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a058

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Amination of nitrobenzene via nucleophilic aromatic substitution for hydrogen: direct formation of aromatic amide bonds

Michael K. Stern, Brian K. Cheng

pp 6883–6888

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a059

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A novel and convenient electrochemical synthesis of 3,7-diaryl-2H-imidazo[2,1-b][1,3,4]oxadiazines

Fructuoso Barba, Belen Batanero

pp 6889–6891

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a060

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Modification of the photochemical reactivity of the cyclic ethylene acetal of .alpha.-bromopropiophenone by adsorption within zeolites. A combined contribution of Lewis acidity and cage effect in the formation of a 2-phenylpropanoate via 1,2-phenyl shift

Avelino Corma, Hermenegildo Garcia, Miguel A. Miranda, Jaime Primo, Maria J. Sabater

pp 6892–6894

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a061

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Novel pendant-type macrocyclic bifunctional chelating agents: (carboxymethyl)amino derivatives of 2-(4-nitrobenzyl)-1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid and their complex formation with yttrium(III)

Kazuya Takenouchi, Masayasu Tabe, Kenzo Watanabe, Atsuo Hazato, Yoshinori Kato, Mitsuhiko Shionoya, Tohru Koike, Eiichi Kimura

pp 6895–6899

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a062

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Synthetic methods and reactions. 188. Triflic acid catalyzed phenylamination of aromatics with phenyl azide

George A. Olah, Pichika Ramaiah, Qi Wang, G. K. Surya Prakash

pp 6900–6901

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a063

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High diastereofacial selectivity in asymmetric Mannich reaction of acyldithiane oxide enolates

Philip C. Bulman Page, Steven M. Allin, Eric W. Collington, Robin A. E. Carr

pp 6902–6904

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a064

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Evidence for intramolecular carbon-hydrogen ...oxygen hydrogen bonds determining N,N'-diacylindigo crystal structure conformations

Bradley D. Smith, Kenneth J. Haller, Maoyu Shang

pp 6905–6907

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a065

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Reduction of benzylic halides with diethylzinc using tetrakis(triphenylphosphine)palladium as catalyst

Konstantinos A. Agrios, Morris Srebnik

pp 6908–6910

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a066

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Cleavage and activation of benzylidene lactones with N-bromosuccinimide

V. D. Reddy, R. W. Franck

pp 6911–6912

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a067

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Direct borohydride reduction of alcohols to alkanes with phosphonium anhydride activation

James B. Hendrickson, Michael Singer, M. Sajjat Hussoin

pp 6913–6914

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a068

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Total synthesis of (.+-.)-(1.beta.,6.alpha.,9.beta.,10.alpha.)-9-chloro-10-hydroxy-8-(methoxycarbonyl)-4-methylene-2,5-dioxabicyclo[4.4.0]dec-7-en-3-one, the first chloride-containing chorismate metabolite from fungi

Cheng Tu, Glenn A. Berchtold

pp 6915–6916

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a069

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Enantioselective Diels-Alder reaction of .alpha.-bromo-.alpha.,.beta.-enals with dienes under catalysis by CAB

Kazuaki Ishihara, Qingzhi Gao, Hisashi Yamamoto

pp 6917–6919

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a070

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.alpha.-Alkoxyacrylic acids from .alpha.-keto acids

Robert B. Bates, Sriyani Caldera

pp 6920–6921

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a071

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1,.omega.-Perfluoroalkylation of aromatics via bis-decarboxylation of perfluorodicarboxylic acids with xenon difluoride

Valery K. Brel, Viktor I. Uvarov, Nikolai S. Zefirov, Peter J. Stang, Ron Caple

pp 6922–6923

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a072

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Polymastiamide A, a novel steroid/amino acid conjugate isolated from the Norwegian marine sponge Polymastia boletiformis (Lamarck, 1815)

Fangming Kong, Raymond J. Andersen

pp 6924–6927

Publication Date: November 1993 (Article)

DOI: 10.1021/jo00076a073

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Amphidinolide K, a new 19-membered macrolide from the cultured symbiotic dinoflagellate Amphidinium sp

Masami Ishibashi, Masaaki Sato, Junichi Kobayashi

pp 6928–6929

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a074

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Reaction of isocyanogen (CNCN) with hydrogen chloride

S. J. Goede, B. L. M. van Baar, F. Bickelhaupt

pp 6930–6931

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a075

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X-ray photoelectron spectral characterization of the extremely electron-deficient nature of .beta.-octakis(N,N-diethylcarboxamido)porphyrin

Abhik Ghosh

p 6932

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a076

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Asymmetric synthesis of (1S,2R)-(+)-2-phenyl-1-aminocyclopropane-1-carboxylic acid

Robert M. Williams, Glenn J. Fegley

pp 6933–6935

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a077

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Synthesis of 2,3-disubstituted and 2,3,6-trisubstituted 1H-indol-5-ols from 3-alkenylphenols

Masato Satomura

pp 6936–6938

Publication Date: November 1993 ()

DOI: 10.1021/jo00076a078

First Page

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