Table of Contents

July 25, 1997
Volume 62, Issue 15
Pages 4896-5240
For Selected Content:

Articles

An Interesting Benzyne-Mediated Annulation Leading to Benzo[a]pyrene

Agustín Cobas, Enrique Guitián, and L. Castedo
pp 4896–4897
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo9706234

Enantioselective Carbolithiation of Cinnamyl Acetals. New Access to Chiral Disubstituted Cyclopropanes

Stephanie Norsikian, Ilane Marek, Jean-François Poisson, and Jean F. Normant
pp 4898–4899
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo9705172

Intramolecular 2 + 2 Cycloaddition in a Baccatin. From a Tetracyclic to a Hexacyclic Molecule

Eldon G. Nidy, Nancy A. Wicnienski, Constance G. Chidester, Paul J. Dobrowolski, Stephen A. Mizsak, Arthur Toy, Thomas A. Runge, Samuel J. Qualls, Robert C. Kelly, and Roy A. Johnson
pp 4900–4901
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo970645q

Solid-Phase Dendrimer Synthesis and the Generation of Super-High-Loading Resin Beads for Combinatorial Chemistry

Vinay Swali, Neil J. Wells, G. John Langley, and Mark Bradley
pp 4902–4903
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo9708654

Grunwald−Winstein Relations in the Solvolyses of Highly Congested Simple Secondary and Tertiary Alkyl Systems. Evidence for the Brønsted Base-Type Solvation in the Standard 1- and 2-Adamantyl Systems

Ken'ichi Takeuchi, Yasushi Ohga, Takuhiro Ushino, and Masaaki Takasuka
pp 4904–4905
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo970709x

Enhancement of the Enantioselectivity in Lipase-Catalyzed Kinetic Resolutions of 3-Phenyl-2H-azirine-2-methanol by Lowering the Temperature to −40 °C

Takashi Sakai, Isamu Kawabata, Tetsuo Kishimoto, Tadashi Ema, and Masanori Utaka
pp 4906–4907
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo970581j

Transition Metal Catalyzed Cycloadditions:  An Intramolecular [4 + 4] Cycloaddition Strategy for the Efficient Synthesis of Dicyclopenta[a,d]cyclooctene 5−8−5 Ring Systems

Paul A. Wender, John M. Nuss, David B. Smith, Angel Suárez-Sobrino, Jan Vågberg, Debra Decosta, and Jon Bordner
pp 4908–4909
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo970841x

Anomalous Products from Intramolecular Insertion Reactions of Rhodium Carbenoids into the α-C−H Bonds of Ethers

J. Stephen Clark and Alexander G. DossetterC. Adam Russell and William G. Whittingham
pp 4910–4911
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo970842p

Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction

James S. Panek and Tao Hu
pp 4912–4913
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo970647a

Asymmetric Synthesis of (2S,3S,8S,9S)-N-Boc ADDA:  Application of a Palladium(0)-Catalyzed Cross-Coupling Reaction of Trisubstituted Olefins

James S. Panek and Tao Hu
pp 4914–4915
Publication Date (Web): July 25, 1997 (Communication)
DOI: 10.1021/jo9706483

Reactions of Alcohols with Cesium Fluoroxysulfate

Stojan Stavber, Iztok Košir, and Marko Zupan
pp 4916–4920
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo962424a

On the Reaction of 3-Bromo-2-nitrobenzo[b]thiophene 13C-Labeled at C-2 with 3-(Trifluoromethyl)aniline:  A Preliminary Insight into a Nucleophilic Substitution with Rearrangement

Domenico Spinelli, Paolo Zanirato, and Elvira Di MiceliLiliana LamartinaFrancesco Guerrera
pp 4921–4923
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo962256m

Conformational Studies by Dynamic NMR. 60.1 Structure and Stereomutation of the Enantiomers of Dialkoxy Disulfides

R. Borghi, L. Lunazzi, and G. PlacucciG. CerioniE. ForestiA. Plumitallo
pp 4924–4927
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970071p

Host Properties of α-Cyclodextrin and a Water-Soluble Calix[6]arene Probed with Dimeric Bipyridinium Guests

René Castro, Luis A. Godínez, Cecil M. Criss, and Angel E. Kaifer
pp 4928–4935
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo9701997

Geometrically Constrained Tetrathiafulvalenophanes:  Synthesis and Characterization

Jesper Lau, Philippe Blanchard, Amédée Riou, Michel Jubault, Michael P. Cava, and Jan Becher
pp 4936–4942
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970326z

Toward a Switchable Molecular Rotor. Unexpected Dynamic Behavior of Functionalized Overcrowded Alkenes

Anne Marie Schoevaars, Wim Kruizinga, Robert W. J. Zijlstra, Nora Veldman, Anthony L. Spek, and Ben L. Feringa
pp 4943–4948
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo962210t

Synthesis of Hydroxy(or Hydroperoxy)-Substituted 1,2,4-Trioxacycloalkanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals

Yoshihiro Ushigoe, Yuko Torao, Araki Masuyama, and Masatomo Nojima
pp 4949–4954
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970555l

Aziridines as Precursors for Chiral Amide-Containing Surfactants

N. A. J. M. Sommerdijk, P. J. J. A. Buynsters, H. Akdemir, D. G. Geurts, R. J. M. Nolte, and B. Zwanenburg
pp 4955–4960
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo962298a

Synthesis of a Reduced Ring Analog of Didemnin B

Joshi M. Ramanjulu, Xiaobin Ding, and Madeleine M. JoulliéWen-Ren Li
pp 4961–4969
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo9623696

Synthesis of a Family of Fine-Tunable New Chiral Ligands for Catalytic Asymmetric Synthesis. Ligand Optimization through the Enantioselective Addition of Diethylzinc to Aldehydes

Anton Vidal-Ferran, Albert Moyano, Miquel A. Pericàs, and Antoni Riera
pp 4970–4982
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo9701445

Cyclization Pathways of a (Z)-Stilbene-Derived Bis(orthoquinone monoketal)

Ken S. Feldman
pp 4983–4990
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo9704220

Acid-Promoted Rearrangement of Cyclic α,β-Epoxy Acylates:  Stereoselective Synthesis of Spirocyclanes and Quaternary Carbon Centers

Yasuyuki Kita, Shinji Kitagaki, Yutaka Yoshida, Sachiko Mihara, Dai-Fei Fang, Michinori Kondo, Sachi Okamoto, Reiko Imai, Shuji Akai, and Hiromichi Fujioka
pp 4991–4997
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970035q

Cycloadditions of Cephalosporins. A Comprehensive Study of the Reaction of Cephalosporin Triflates with Olefins, Acetylenes, and Dienes To Form [2 + 2] and [4 + 2] Adducts

Richard L. Elliott, Neville H. Nicholson, Fiona E. Peaker, Andrew K. Takle, Christine M. Richardson, John W. Tyler, Janet White, Michael J. Pearson, Drake S. Eggleston, and R. Curtis Haltiwanger
pp 4998–5016
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970176s

Absolute Configuration of Chiral Ethanol-1-d:  Neutron Diffraction Analysis of the (−)-(1S)-Camphanate Ester of (+)-(R)-Ethanol-1-d

Tobias Metzenthin, André Schreiber, Richard K. McMullan, Thomas F. Koetzle, Harry S. Mosher, and Robert Bau
pp 5017–5022
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970615n

Applications of Organosulfur Chemistry to Organic Synthesis:  Total Synthesis of (+)-Himbeline and (+)-Himbacine

David J. Hart, Jing Li, and Wen-Lian WuAlan P. Kozikowski
pp 5023–5033
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970612a

Synthetic and Computational Studies on Symmetry-Defined Double Cycloaddition of a New Tris-Annulating Reagent to C60

Hiroyuki Isobe, Hidetoshi Tokuyama, Masaya Sawamura, and Eiichi Nakamura
pp 5034–5041
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970685u

First Synthesis of Exomethylene Paracyclophanes and Their Structural Properties

Shinichi Saito, Norie Tsuboya, and Yoshinori Yamamoto
pp 5042–5047
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970727e

Enantioselective Construction of Cyclic Ethers by An Aldol-Cyclization Sequence

Paul Galatsis, Scott D. Millan, and George Ferguson
pp 5048–5056
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo961904z

Nonionic Superbase-Catalyzed Silylation of Alcohols

Bosco A. D'Sa, Dale McLeod, and John G. Verkade
pp 5057–5061
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo9701492

Studies toward the Synthesis of Vinigrol. First Construction of the Tricyclic Ring System

Jean-François Devaux, Issam Hanna, and Jean-Yves Lallemand
pp 5062–5068
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970343o

Cyclopropanation/Reduction of a 3,4-Disubstituted 2(5H)-Furanone:  A Model for C-8 Methylation at the Taxane BC Ring Juncture

Thomas E. Janini and Paul Sampson
pp 5069–5073
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970564u

High-Resolution Solid State 19F and 15N MAS NMR Spectra of Fluoroaromatics and Aromatic Nitrogen Heterocycles Physisorbed on Silica and Alumina

Gero von Fircks, Heike Hausmann, Volkhard Francke, and Harald Günther
pp 5074–5079
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo961104o

Conformational Complexity in Seven-Membered Cyclic Triazepinone/Open Hydrazones. 1. 1D and 2D Variable Temperature NMR Study

Kalevi Pihlaja, Mario F. Simeonov, and Ferenc Fülöp
pp 5080–5088
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo962322k

Conformational Complexity in Seven-Membered Cyclic Triazepinone/Open Hydrazones. 2. Molecular Modeling and X-ray Study

Mario F. Simeonov, Ferenc Fülöp, Reijo Sillanpää, and Kalevi Pihlaja
pp 5089–5095
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo962323c

Transacetalization with Acylium Ions. A Structurally Diagnostic Ion/Molecule Reaction for Cyclic Acetals and Ketals in the Gas Phase

Luiz Alberto B. Moraes, Fábio C. Gozzo, and Marcos N. EberlinPirjo Vainiotalo
pp 5096–5103
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970116m

An Experimental and Theoretical Study on the Prototropic Equilibria of the Four Carboline Isomers

Gonzalo Angulo, Carmen Carmona, Rafael R. Pappalardo, María A. Muñoz, Pilar Guardado, Enrique Sánchez Marcos, and Manuel Balón
pp 5104–5109
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970130z

Effects of Substituents in the 3-Position on the [2 + 2] Pentadienyl Cation Electrocyclization1

Douglas A. Smith and Charles W. Ulmer, II
pp 5110–5115
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo9703313

Dendritic Bis(oxazoline)copper(II) Catalysts. 2.1 Synthesis, Reactivity, and Substrate Selectivity

Hak-Fun Chow and Chi Ching Mak
pp 5116–5127
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970383s

Correlation of Oxidation and Ionization Potentials for Azoalkanes

Werner M. Nau, Waldemar Adam, Dieter Klapstein, Coskun Sahin, and Herbert Walter
pp 5128–5132
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970574v

A Novel Synthetic Route to Sapphyrins

Roberto Paolesse, Silvia Licoccia, Mariangela Spagnoli, Tristano Boschi, Richard G. Khoury, and Kevin M. Smith
pp 5133–5137
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo9704117

Stereospecific Synthesis of cis-2-Alkoxy-3-aminooxolanes

Norbert De Kimpe, Wim Aelterman, and Koen De GeyterJean-Paul Declercq
pp 5138–5143
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970410e

Formaldehyde Dialkylhydrazones as Neutral Formyl Anion and Cyanide Equivalents:  Nucleophilic Addition to Conjugated Enones

Elena Díez, Rosario Fernández, Consolación Gasch, José M. Lassaletta, José M. Llera, Eloísa Martín-Zamora, and Juan Vázquez
pp 5144–5155
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970481d

Solution Phase Combinatorial Chemistry. Synthesis of Novel Linear Pyridinopolyamine Libraries with Potent Antibacterial Activity

Haoyun An, Becky D. Haly, Allister S. Fraser, Charles J. Guinosso, and P. Dan Cook
pp 5156–5164
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970535j

An Approach to Photolabile, Fluorescent Protecting Groups

Kevin Burgess, Swanee E. Jacutin, Dongyeol Lim, and Aroonsiri Shitangkoon
pp 5165–5168
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo9702608

Conformationally Restrained Chiral Analogues of Spermine:  Chemical Synthesis and Improvements in DNA Triplex Stability

Kallanthottathil G. Rajeev, Gangadhar J. Sanjayan, and Krishna N. Ganesh
pp 5169–5173
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970414j

Synthesis of Functionalized Aromatic Oligomers from a Versatile Diphenylmethane Template

J. G. Bruno, M. N. Chang, Y. M. Choi-Sledeski, D. M. Green, D. G. McGarry, J. R. Regan, and F. A. Volz
pp 5174–5190
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo970596h

Mechanism of Acid-Catalyzed Epoxidation of Alkenes with Peroxy Acids

Robert D. Bach, Carlo Canepa, Julia E. Winter, and Paul E. Blanchette
pp 5191–5197
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo950930e

Hartree−Fock and Møller−Plesset (MP2) Treatment of Oxygen-Containing Phosphorus Compounds

Eugene L. Stewart, Neysa Nevins, Norman L. Allinger, and J. Phillip Bowen
pp 5198–5207
Publication Date (Web): July 25, 1997 (Article)
DOI: 10.1021/jo961212a

Determination of the Enantiomerization Barrier of Arylnaphthalene Lignans by Cryogenic Subcritical Fluid Chromatography and Computer Simulation

Christian Wolf, William H. Pirkle, Christopher J. Welch, Detlev H. Hochmuth, Wilfried A. König, Gaik-Lean Chee, and James L. Charlton
pp 5208–5210
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo9623705

A Facile Access to Densely Functionalized Substituted Cyclopentanes and Spiro Cyclopentanes. Carbocation Stabilization Directed Bond Migration in Rearrangement of Cyclobutanes

Azizul Haque, Anjan Ghatak, Subrata Ghosh, and Nanda Ghoshal
pp 5211–5214
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo970283m

Enantiodivergent Chemoenzymatic Synthesis of (R)- and (S)-β-Proline in High Optical Purity

Claudio Mazzini, Jacques Lebreton, Véronique Alphand, and Roland Furstoss
pp 5215–5218
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo9701905

Short Asymmetric Synthesis of (+)-α-Curcumene and (+)-Xanthorrhizol

A. I. Meyers and Diana Stoianova
pp 5219–5221
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo970429h

Synthesis of 2-Alkylbenzimidazoles via TiO2-Mediated Photocatalysis

Hongyu Wang, Richard E. Partch, and Yuzhuo Li
pp 5222–5225
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo970253j

(1R,2S)-(+)-cis-1-Amino-2-indanol:  An Effective Ligand for Asymmetric Catalysis of Transfer Hydrogenations of Ketones

Matthew Palmer, Tim Walsgrove, and Martin Wills
pp 5226–5228
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo970405a

Reaction of Halogenated Cyclopropanes and Nitrosyl Cation:  Preparation of Isoxazoles

Shaw-Tao Lin, Shing-Huey Kuo, Fu-May Yang
pp 5229–5231
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo962297i

Cyclopropane Formation vs the Homoallyl−Homoallyl Radical Rearrangement in 7-Oxygen-Substituted Norborn-5-en-2-yl Radicals

A. Srikrishna, R. Viswajanani, T. Jagadeeswar Reddy, D. Vijaykumar, and P. Praveen Kumar
pp 5232–5234
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo970246v

Selective Monoalkylation of Diethyl Malonate, Ethyl Cyanoacetate, and Malononitrile Using a Masking Group for the Second Acidic Hydrogen

Robert B. Grossman and Melissa A. Varner
pp 5235–5237
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo9708248

Arabinonucleotide Synthesis by the Epoxide Route

C. D. Roussev, M. F. Simeonov, and D. D. Petkov
pp 5238–5240
Publication Date (Web): July 25, 1997 (Note)
DOI: 10.1021/jo970292v

Synthesis of an Enantiomerically Pure Serine-Derived Thiazole

Jennifer A. Sowinski and Peter L. Toogood
p 5240
Publication Date (Web): July 25, 1997 (Addition/Correction)
DOI: 10.1021/jo974008b
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