Table of Contents

May 4, 2001
Volume 66, Issue 9
Pages 2891-3248

About the Cover: The year 2001 marks the centennial of the discovery of the first long-lived carbocation, the triphenylmethyl cation. The field has come a long way following the discovery by Olah of methods to prepare long-lived (persistent) stable carbocations in superacid medium. The cover shows several structurally diverse classes of carbenium ions, including alkyl mono- and dications and five and higher coordinate carbonium mono- and dications encompassing two-electron three-center bonding. See Olah and co-workers, p 2907. View the article.

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Articles

Spirodienone Derivatives of a Spherand-Type Calixarene

Kasim Agbaria, Oleg Aleksiuk, Silvio E. Biali, Volker Böhmer, Michael Frings, and Iris Thondorf
pp 2891–2899
Publication Date (Web): April 10, 2001 (Article)
DOI: 10.1021/jo001648x

Stereochemistry of a Spherand-Type Calixarene

Kasim Agbaria, Silvio E. Biali, Volker Böhmer, Jörg Brenn, Shmuel Cohen, Michael Frings, Flavio Grynszpan, Jack McB. Harrowfield, Alexander N. Sobolev, and Iris Thondorf
pp 2900–2906
Publication Date (Web): April 10, 2001 (Article)
DOI: 10.1021/jo0016576

Gitonic and Distonic Alkanonium Dications (Diprotonated Alkane Dications CnH2n+42+, n = 1−4)1

George. A. Olah, G. K. Surya Prakash, and Golam Rasul
pp 2907–2910
Publication Date (Web): February 23, 2001 (Article)
DOI: 10.1021/jo001452x

Photooxygenation of the Helimers of (−)-Isocolchicine:  Regio- and Facial Selectivity of the [4 + 2] Cycloaddition with Singlet Oxygen and Surprising Endoperoxide Transformations

René Brecht, Frank Büttner, Markus Böhm, Gunther Seitz, Gerlinde Frenzen, Astrid Pilz, and Werner Massa
pp 2911–2917
Publication Date (Web): April 05, 2001 (Article)
DOI: 10.1021/jo991171t

Electronic Delocalization Contribution to the Anomeric Effect Evaluated by Computational Methods

Fernando Cortés, Julieta Tenorio, Ofelia Collera, and Gabriel Cuevas
pp 2918–2924
Publication Date (Web): March 31, 2001 (Article)
DOI: 10.1021/jo000560g

Rigorous Interpretation of Electronic Density Functions of Axial and Equatorial Conformers of Dimethylphosphinoylcyclohexane, 2-(Dimethylphosphinoyl)-1,3,5-trithiane, and 2-(Dimethylphosphinoyl)-1,3-dithiane-1,1,3,3-tetraoxide

Gustavo Madrid, Ana Rochín, Eusebio Juaristi, and Gabriel Cuevas
pp 2925–2931
Publication Date (Web): March 31, 2001 (Article)
DOI: 10.1021/jo001505a

Synthesis of Benzonorbornadienes:  Regioselective Benzyne Formation

Kenneth C. Caster, Christopher G. Keck, and Russell D. Walls
pp 2932–2936
Publication Date (Web): April 03, 2001 (Article)
DOI: 10.1021/jo001277k

2‘-Ribose-Ferrocene Oligonucleotides for Electronic Detection of Nucleic Acids

C. J. Yu, Hai Wang, Yanjian Wan, Handy Yowanto, Joseph C. Kim, Leslee H. Donilon, Chunlin Tao, Michael Strong, and Yoochul Chong
pp 2937–2942
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo001283g

Flash Vacuum Pyrolysis over Solid Catalysts. 1. Pyrazoles over Zeolites

Elizabeth L. Moyano and Gloria I. Yranzo
pp 2943–2947
Publication Date (Web): April 11, 2001 (Article)
DOI: 10.1021/jo001390a

Chemoenzymatic Synthesis of Neoglycopeptides:  Application to an α-Gal-Terminated Neoglycopeptide

Delphine Ramos, Patrick Rollin, and Werner Klaffke
pp 2948–2956
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo001439c

Use of Fluorobenzoyl Protective Groups in Synthesis of Glycopeptides:  β-Elimination of O-Linked Carbohydrates Is Suppressed

Petter Sjölin and Jan Kihlberg
pp 2957–2965
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo001584q

Synthesis and Characterization of Photoswitchable Lipids Containing Hemithioindigo Chromophores

Keetah Eggers, Thomas M. Fyles, and Pedro J. Montoya-Pelaez
pp 2966–2977
Publication Date (Web): April 05, 2001 (Article)
DOI: 10.1021/jo0056848

Molecular Design and Synthesis of Artificial Ion Channels Based on Cyclic Peptides Containing Unnatural Amino Acids

Hitoshi Ishida, Zhi Qi, Masahiro Sokabe, Kiyoshi Donowaki, and Yoshihisa Inoue
pp 2978–2989
Publication Date (Web): April 03, 2001 (Article)
DOI: 10.1021/jo001079t

Generation of Reactive Low-Valent Titanium Species Using Μetal−Αrenes as Efficient Organic Reductants for TiCl3:  Applications to Organic Synthesis

Shyam Rele, Sanjay Talukdar, Asoke Banerji, and Subrata Chattopadhyay
pp 2990–2994
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo001586a

The Photochemistry of 2-(1-Naphthyl)ethyl Benzoates:  Cycloaddition and Intramolecular Exciplex Formation

Krista Morley and James A. Pincock
pp 2995–3003
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo001633z

Practical Cobalt Carbonyl Catalysis in the Thermal Pauson−Khand Reaction:  Efficiency Enhancement Using Lewis Bases

Marie E. Krafft, Llorente V. R. Boñaga, and Chitaru Hirosawa
pp 3004–3020
Publication Date (Web): April 11, 2001 (Article)
DOI: 10.1021/jo0057708

Quantitative Calculations of Antibody−Antigen Binding:  Steroid−DB3 Binding Energies by the Linear Interaction Energy Method

Jiangang Chen, Renxiao Wang, Michael Taussig, and K. N. Houk
pp 3021–3026
Publication Date (Web): April 10, 2001 (Article)
DOI: 10.1021/jo001619m

Modular Synthesis of π-Acceptor Cyclophanes Derived from 1,4,5,8-Naphthalenetetracarboxylic Diimide and 1,5-Dinitronaphthalene

Guoying Chen, John T. Lean, Monica Alcalá, and Thomas E. Mallouk
pp 3027–3034
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo991054y

Design and Synthesis of Novel Chiral Dendritic Species Derived from Bile Acids

R. Balasubramanian and Uday Maitra
pp 3035–3040
Publication Date (Web): April 05, 2001 (Article)
DOI: 10.1021/jo0013305

Molecular Basis for Enantioselectivity of Lipase from Chromobacterium viscosum toward the Diesters of 2,3-Dihydro-3-(4‘-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol

David G. Gascoyne, Herman L. Finkbeiner, Kwok P. Chan, Janet L. Gordon, Kevin R. Stewart, and Romas J. Kazlauskas
pp 3041–3048
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo005681v

A Stereospecific Synthesis of Oxazolinyloxiranes

Alessandro Abbotto, Vito Capriati, Leonardo Degennaro, Saverio Florio, Renzo Luisi, Marcel Pierrot, and Antonio Salomone
pp 3049–3058
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo0057607

Lithiated 4-Isopropyl-3-(methylthiomethyl)-5,5-diphenyloxazolidin-2-one:  A Chiral Formyl Anion Equivalent for Enantioselective Preparations of 1,2-Diols, 2-Amino Alcohols, 2-Hydroxy Esters, and 4-Hydroxy-2-alkenoates

Christoph Gaul, Kaspar Schärer, and Dieter Seebach
pp 3059–3073
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo0155254

Synthesis of Phosphorylated and Sulfated Glycosyl Serines in the Linkage Region of the Glycosaminoglycans

Jun-ichi Tamura and Junko Nishihara
pp 3074–3083
Publication Date (Web): April 07, 2001 (Article)
DOI: 10.1021/jo001540h

Stereoselective and Regioselective Reaction of Cyclic Ortho Esters with Phenols

Joseph J. Bozell, Darrin Miller, Bonnie R. Hames, and Cheryl Loveless
pp 3084–3089
Publication Date (Web): April 06, 2001 (Article)
DOI: 10.1021/jo005736t

The Secondary Amine/Nitric Oxide Complex Ion R2N[N(O)NO]- as Nucleophile and Leaving Group in SNAr Reactions

Joseph E. Saavedra, Aloka Srinivasan, Challice L. Bonifant, Jingxi Chu, Anna P. Shanklin, Judith L. Flippen-Anderson, William G. Rice, Jim A. Turpin, Keith M. Davies, and Larry K. Keefer
pp 3090–3098
Publication Date (Web): April 11, 2001 (Article)
DOI: 10.1021/jo0016529

Significant Acceleration of 6π-Azaelectrocyclization Resulting from a Remarkable Substituent Effect and Formal Synthesis of the Ocular Age Pigment A2-E by a New Method for Substituted Pyridine Synthesis

Katsunori Tanaka, Hajime Mori, Mako Yamamoto, and Shigeo Katsumura
pp 3099–3110
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo005779+

Approaches to the Synthesis of Some Tyrosine-Derived Marine Sponge Metabolites:  Synthesis of Verongamine and Purealidin N

Todd R. Boehlow, J. Jonathan Harburn, and Christopher D. Spilling
pp 3111–3118
Publication Date (Web): March 30, 2001 (Article)
DOI: 10.1021/jo010015v

Application of Furanyl Carbamate Cycloadditions Toward the Synthesis of Hexahydroindolinone Alkaloids

Albert Padwa, Michael A. Brodney, Martin Dimitroff, Bing Liu, and Tianhua Wu
pp 3119–3128
Publication Date (Web): April 04, 2001 (Article)
DOI: 10.1021/jo010020z

Concerted Mechanisms of the Reactions of Methyl Aryl Carbonates with Substituted Phenoxide Ions

Enrique A. Castro, Paulina Pavez, and José G. Santos
pp 3129–3132
Publication Date (Web): April 05, 2001 (Article)
DOI: 10.1021/jo010022j

Enantioselective Synthesis of the AB-Ring System of the Antitumor Antibiotic Tetrazomine

Peter Wipf and Corey R. Hopkins
pp 3133–3139
Publication Date (Web): March 28, 2001 (Article)
DOI: 10.1021/jo015512q

Use of a Methoxy Substituent in Controlling the Stereochemistry of Intramolecular Iron-Mediated Diene/Olefin Cyclocoupling

Anthony J. Pearson and Ismet B. Dorange
pp 3140–3145
Publication Date (Web): April 06, 2001 (Article)
DOI: 10.1021/jo010035x

Synthesis of New Optically Active Propargylic Fluorides and Application to the Enantioselective Synthesis of Monofluorinated Analogues of Fatty Acid Metabolites

Michaël Prakesch, Danielle Grée, and René Grée
pp 3146–3151
Publication Date (Web): April 07, 2001 (Article)
DOI: 10.1021/jo010056r

Porphyrins with Exocyclic Rings. 16.1 Synthesis and Spectroscopic Characterization of Fluoranthoporphyrins, a New Class of Highly Conjugated Porphyrin Chromophores

Timothy D. Lash, Tonya M. Werner, Michelle L. Thompson, and Jerad M. Manley
pp 3152–3159
Publication Date (Web): April 11, 2001 (Article)
DOI: 10.1021/jo010066s

Poly(ethylene glycol)-Supported Bisoxazolines as Ligands for Catalytic Enantioselective Synthesis

Rita Annunziata, Maurizio Benaglia, Mauro Cinquini, Franco Cozzi, and Manuela Pitillo
pp 3160–3166
Publication Date (Web): April 06, 2001 (Article)
DOI: 10.1021/jo010077l

Synthesis of Polycyclic Guanidines by Cyclocondensation Reactions of N-Amidinyliminium Ions

Larry E. Overman and John P. Wolfe
pp 3167–3175
Publication Date (Web): April 12, 2001 (Article)
DOI: 10.1021/jo0100998

Intramolecular [4 + 2] Cycloaddition Reaction of Six- and Seven-Membered Cyclic N-Allyl-C-arylethynyl Iminium Salts

Hans-Georg Herz, Jürgen Schatz, and Gerhard Maas
pp 3176–3181
Publication Date (Web): April 11, 2001 (Article)
DOI: 10.1021/jo015546y

Biradical Intermediates in the Photoisomerization of Dibenzodihydropentalenofurans to Dibenzosemibullvalenes1

Meledathu C. Sajimon, Danaboyina Ramaiah, Kakkudiyil G. Thomas, and Manapurathu V. George
pp 3182–3187
Publication Date (Web): March 23, 2001 (Article)
DOI: 10.1021/jo0101353

Steps To Demarcate the Effects of Chromophore Aggregation and Planarization in Poly(phenyleneethynylene)s. 2. The Photophysics of 1,4-Diethynyl-2-fluorobenzene in Solution and in Crystals

Marcia Levitus, Gerardo Zepeda, Hung Dang, Carlos Godinez, Tinh-Alfredo V. Khuong, Kelli Schmieder, and Miguel A. Garcia-Garibay
pp 3188–3195
Publication Date (Web): April 04, 2001 (Article)
DOI: 10.1021/jo015589e

Notes

Determination of the Nucleophilicities of N,N-Bis(silyloxy)enamines

Alexander D. Dilman, Sema L. Ioffe, and Herbert Mayr
pp 3196–3200
Publication Date (Web): April 12, 2001 (Note)
DOI: 10.1021/jo0015927

Stereoselective Access to Hydroxy Oxetanes and Tetrahydrooxepines through Isomerization of Oxiranyl Ethers

Alessandro Mordini, Simona Bindi, Antonella Capperucci, Daniele Nistri, Gianna Reginato, and Michela Valacchi
pp 3201–3205
Publication Date (Web): April 11, 2001 (Note)
DOI: 10.1021/jo0005924

New Access to C-Branched Sugars and C-Disaccharides under Indium Promoted Barbier-type Allylations in Aqueous Media

Yves Canac, Eric Levoirier, and André Lubineau
pp 3206–3210
Publication Date (Web): April 03, 2001 (Note)
DOI: 10.1021/jo001217e

A Theoretical Study of the Molecular Mechanism of the Reaction between N,N-Dimethylmethyleneammonium Cation and Cyclopentadiene

Luis R. Domingo
pp 3211–3214
Publication Date (Web): April 04, 2001 (Note)
DOI: 10.1021/jo001332p

Linear versus Y-Topology in Conjugated Polyene Dications:  Questioning Y-Aromaticity

T. P. RadhakrishnanIsrael Agranat
pp 3215–3219
Publication Date (Web): April 06, 2001 (Note)
DOI: 10.1021/jo0015016

Electrophilic Azidation for Stereoselective Synthesis of 2-Azido-2-deoxyaldono-1,5-lactones

J. S. Dileep Kumar, François-Yves Dupradeau, M. Jane Strouse, Michael E. Phelps, and Tatsushi Toyokuni
pp 3220–3223
Publication Date (Web): March 29, 2001 (Note)
DOI: 10.1021/jo005728c

Asymmetric Synthesis of a New 8-Hydroxyquinoline-Derived α-Amino Acid and Its Incorporation in a Peptidylsensor for Divalent Zinc

Nathalie Jotterand, Dierdre A. Pearce, and Barbara Imperiali
pp 3224–3228
Publication Date (Web): March 29, 2001 (Note)
DOI: 10.1021/jo001681j

Diphenylacetylene and the LICKOR Superbase:  o,o‘-Dimetalation and Reaction with Electrophiles. A Convenient Synthesis of o,o‘-Disubstituted Diphenylacetylenes

Janusz Kowalik and Laren M. Tolbert
pp 3229–3231
Publication Date (Web): April 12, 2001 (Note)
DOI: 10.1021/jo001533t

Oxidation of Organic Sulfides by Br2 and H2O2. Electrophilic and Free-Radical Processes

Anna Bravo, Barbara Dordi, Francesca Fontana, and Francesco Minisci
pp 3232–3234
Publication Date (Web): April 11, 2001 (Note)
DOI: 10.1021/jo0017178

Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na2WO4, Na2VO4, or Na2MoO4 under Organic Solvent-Free Conditions

Min Shi and Yan-Shu Feng
pp 3235–3237
Publication Date (Web): April 11, 2001 (Note)
DOI: 10.1021/jo001796n

Highly Regio- and Enantioselective Palladium-Catalyzed Allylic Amination with Sodium Diformylamide

Yi Wang and Kuiling Ding
pp 3238–3241
Publication Date (Web): April 07, 2001 (Note)
DOI: 10.1021/jo015553m

Synthesis of the C1‘−C11‘ Segment of Leucascandrolide A

Peter Wipf and Thomas H. Graham
pp 3242–3245
Publication Date (Web): April 12, 2001 (Note)
DOI: 10.1021/jo005787q

Deoxyamphimedine, a New Pyridoacridine Alkaloid from Two Tropical Xestospongia Sponges

Deniz Tasdemir, Kathryn M. Marshall, Gina C. Mangalindan, Gisela P. Concepción, Louis R. Barrows, Mary Kay Harper, and Chris M. Ireland
pp 3246–3248
Publication Date (Web): April 11, 2001 (Note)
DOI: 10.1021/jo010153k
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