Organic Chemistry : Structure and Mechanisms.

367 Pages·2011·6.27 MB·English

Research Progress in Chemistry
Organic Chemistry T
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Structure and Mechanisms
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This book presents a range of research on important topics in the field. Of the approximately 11 Organic Chemistry
million known chemical compounds, about 10 million are organic. Organic chemists are currently
working to produce better polymers with specific properties, such as biodegradable plastics. The
understanding of new drug structures from plants and the synthesis of improved pharmaceuticals
is another area of great interest. organic chemists are also researching the reactions that occur in
Structure and Mechanisms
living systems and understanding the molecular causes of disease.
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About the Editor
Dr. Harold H. Trimm was born in 1955 in Brooklyn, New York. Dr. Trimm is the chairman of the
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Chemistry Department at Broome Community College in Binghamton, New York. In addition, he is g
an Adjunct Analytical Professor, Binghamton University, State University of New York, S
Binghamton, New York. t a
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He received his PhD in chemistry, with a minor in biology, from Clarkson University in 1981 for his c n
work on fast reaction kinetics of biologically important molecules. He then went on to Brunel tu
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University in England for a postdoctoral research fellowship in biophysics, where he studied the re c
molecules involved with arthritis by electroptics. He recently authored a textbook on forensic a

science titled Forensics the Easy Way (2005). n C
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Other Titles in the Series e
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e
• Analytical Chemistry: Methods and Applications h
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• Inorganic Chemistry: Reactions, Structure and Mechanisms n m
• Physical Chemistry: Chemical Kinetics and Reaction Mechanisms is
m
i
Related Titles of Interest s s
• Environmental Chemistry: New Techniques and Data t
• Industrial Chemistry: New Applications, Processes and Systems r
• Recent Advances in Biochemistry y
ISBN 978-1-926692-60-9 Harold H. Trimm,
00000 PhD
Apple Editor
Apple Academic Press
Academic
www.appleacademicpress.com 9781926692609 Press
Organic chemistry
Structure and Mechanisms
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Research Progress in Chemistry
Organic chemistry
Structure and Mechanisms
Harold H. Trimm, PhD, RSO
Chairman, Chemistry Department, Broome Community College;
Adjunct Analytical Professor, Binghamton University,
Binghamton, New York, U.S.A.
Apple Academic Press
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Version Date: 20120813
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cOntents
Introduction 9
1. Mechanistic Aspects of the Isomerization of Z-Vinylic Tellurides 11
Double Bonds in the Synthesis of Potassium Z-Vinyltrifluoroborate
Salts
Hélio A. Stefani, Rafael C. Guadagnin, Artur F. Keppler,
Giancarlo V. Botteselle, João V. Comasseto and Carlos A. Suganuma
2. The Role of Heterogeneous Chemistry of Volatile Organic 19
Compounds: A Modeling and Laboratory Study
Gregory R. Carmichael and Vicki H. Grassian
3. Total Synthesis of the Indolizidine Alkaloid Tashiromine 27
Stephen P. Marsden and Alison D. McElhinney
4. Application of Stir Bar Sorptive Extraction to Analysis of Volatile 37
and Semivolatile Organic Chemicals of Potential Concern in Solids
and Aqueous Samples from the Hanford Site
J. M. Frye and J. M. Kunkel
5. Analogues of Amphibian Alkaloids: Total Synthesis of 49
(5R,8S,8as)-(-)-8-Methyl-5-Pentyloctahydroindolizine
(8-Epi-Indolizidine 209B) and [(1S,4R,9as)-(-) -4-
Pentyloctahydro-2H-Quinolizin-1-Yl]Methanol
Joseph P. Michael, Claudia Accone, Charles B. de Koning and
Christiaan W. van der Westhuyzen
6 Organic Chemistry: Structure and Mechanisms
6. An Efficient Preparation, Spectroscopic Properties, and Crystal 60
Structure of 1,1-Bis(4-[2-(dimethylamino)ethoxy]phenyl)-2-
(3-guaiazulenyl)ethylene
Shin-ichi Takekuma, Seiki Hori, Toshie Minematsu and
Hideko Takekuma
7. Characterizing the Formation of Secondary Organic Aerosols 69
Melissa Lunden, Douglas Black and Nancy Brown
8. Combining Two-Directional Synthesis and Tandem Reactions, 102
Part 11: Second Generation Syntheses of (±)-Hippodamine and
(±)-Epi-Hippodamine
Annabella F. Newton, Martin Rejzek, Marie-Lyne Alcaraz and
Robert A. Stockman
9. Accelerations in the Lactonization of Trimethyl Lock Systems are 109
Due to Proximity Orientation and not to Strain Effects
Rafik Karaman
10. Unexpected Degradation of the Bisphosphonate P-C-P Bridge 121
Under Mild Conditions
P. A. Turhanen and J. J. Vepsäläinen
11. Synthesis of Benzo[b]fluorenone Nuclei of Stealthins 129
Sujit Kumar Ghorai, Saroj Ranjan De, Raju Karmakar,
Nirmal Kumar Hazra and Dipakranjan Mal
12. Shape-Persistent Macrocycles with Intraannular Alkyl Groups: 140
Some Structural Limits of Discotic Liquid Crystals with an
Inverted Structure
S. Höger, J. Weber, A. Leppert and V. Enkelmann
13. Part 1. Reduction of S-Alkyl-Thionocarbonates and Related 151
Compounds in the Presence of Trialkylboranes/Air
Jean Boivin and Van Tai Nguyen
14. Part 2. Mechanistic Aspects of the Reduction of S-Alkyl- 161
Thionocarbonates in the Presence of Triethylborane and Air
Florent Allais, Jean Boivin and Van Tai Nguyen
15. Part 3. Triethylborane-Air: A Suitable Initiator for Intermolecular 171
Radical Additions of S-2-Oxoalkyl-Thionocarbonates (S-Xanthates)
to Olefins
Jean Boivin and Van Tai Nguyen
Contents 7
16. Catalytic Oxidative Cleavage of C=N Bond in the Presence of 181
Zeolite H-NaX Supported Cu(NO ) , as a Green Reagent
3 2
A. Lalitha, K. Sivakumar, K. Parameswaran, K. Pitchumani and
C. Srinivasan
17. A Divergent Asymmetric Approach to Aza-Spiropyran Derivative 188
and (1S,8ar)-1-Hydroxyindolizidine
Jian-Feng Zheng, Wen Chen, Su-Yu Huang, Jian-Liang Ye and
Pei-Qiang Huang
18. Flexible Synthesis of Poison-Frog Alkaloids of the 197
5,8-Disubstituted Indolizidine-Class. II: Synthesis of (-)-209B,
(-)-231C, (-)-233D, (-)-235B”, (-)-221I, and an Epimer of 193E
and Pharmacological Effects at Neuronal Nicotinic Acetylcholine
Receptors
Soushi Kobayashi, Naoki Toyooka, Dejun Zhou, Hiroshi Tsuneki,
Tsutomu Wada, Toshiyasu Sasaoka, Hideki Sakai, Hideo Nemoto,
H. Martin Garraffo, Thomas F. Spande and John W. Daly
19. A Novel, One-Step Palladium and Phenylsilane Activated Amidation 207
from Allyl Ester on Solid Support
Zheming Ruan, Katy Van Kirk, Christopher B. Cooper and
R. Michael Lawrence
20. The First Organocatalytic Carbonyl-Ene Reaction: Isomerisation- 214
Free C-C Bond Formations Catalysed By H-Bonding Thio-Ureas
Matthew L. Clarke, Charlotte E. S. Jones and Marcia B. France
21. Synthesis and Biological Evaluation of 7-O-Modified 221
Formononetin Derivatives
Ying Yang, Wen-Jun Mao, Huan-Qiu Li, Tao-Tao Zhu, Lei Shi,
Peng-Cheng Lv and Hai-Liang Zhu
22. Expedient Syntheses of the N-Heterocyclic Carbene Precursor 229
Imidazolium Salts Ipr·Hcl, Imes·Hcl and Ixy·Hcl
Lukas Hintermann
23. CS CO /[bmim]Br as an Efficient, Green, and Reusable 239
2 3
Catalytic System for the Synthesis of N-Alkyl Derivatives of
Phthalimide under Mild Conditions
Alireza Hasaninejad, Abdolkarim Zare, Ahmad Reza Moosavi-Zare,
Fatemeh Khedri, Rahimeh Rahimi and Ali Khalafi-Nezhad
8 Organic Chemistry: Structure and Mechanisms
24. Conformational Rigidity of Silicon-Stereogenic Silanes in 248
Asymmetric Catalysis: A Comparative Study
Sebastian Rendler and Martin Oestreich
25. Photochromism of Dihydroindolizines Part XI: Synthesis of 255
Novel Carbon-Rich Photochromic Dihydroindolizines-Based
Potential Electronic Devices
Saleh Abdel-Mgeed Ahmed
26. 8-Epi-Salvinorin B: Crystal Structure and Affinity at the K Opioid 264
Receptor
Thomas A. Munro, Katharine K. Duncan, Richard J. Staples, Wei Xu,
Lee-Yuan Liu-Chen, Cécile Béguin, William A. Carlezon Jr.
and Bruce M. Cohen
27. Effect of Transannular Interaction on the Redox-Potentials in a 271
Series of Bicyclic Quinones
Grigoriy Sereda, Jesse Van Heukelom, Miles Koppang,
Sudha Ramreddy and Nicole Collins
28. Three-Component One-Pot Synthesis of Novel Benzo[b]
1,8-naphthyridines Catalyzed by Bismuth(III) Chloride 285
Tangali R. Ravikumar Naik, Halehatty S. Bhojya Naik,
Halehatty R. Prakasha Naik and P. J. Bindu
29. The Vicinal Difluoro Motif: The Synthesis and Conformation of 293
Erythro- and Threo-Diastereoisomers of 1,2-Difluorodiphenylethanes,
2,3-Difluorosuccinic Acids and their Derivatives
David O’Hagan, Henry S. Rzepa, Martin Schüler and
Alexandra M. Z. Slawin
30. The Influence of Traffic and Wood Combustion on the Stable 315
Isotopic Composition of Carbon Monoxide
M. Saurer, A. S. H. Prévôt, J. Dommen, J. Sandradewi,
U. Baltensperger and R. T. W. Siegwolf
31. Reduction of Arenediazonium Salts by Tetrakis(Dimethylamino) 347
Ethylene (TDAE): Efficient Formation of Products Derived
from Aryl Radicals
Mohan Mahesh, John A. Murphy, Franck LeStrat and
Hans Peter Wessel
Index 366
intrOductiOn
Chemistry is the science that studies atoms and molecules along with their prop-
erties. All matter is composed of atoms and molecules, so chemistry is all encom-
passing and is referred to as the central science because all other scientific fields
use its discoveries. Since the science of chemistry is so broad, it is normally broken
into fields or branches of specialization. The five main branches of chemistry are
analytical, inorganic, organic, physical, and biochemistry. Chemistry is an ex-
perimental science that is constantly being advanced by new discoveries. It is the
intent of this collection to present the reader with a broad spectrum of articles in
the various branches of chemistry that demonstrates key developments in these
rapidly changing fields.
Organic chemistry is the study of compounds that contain the element car-
bon. Carbon is unique among the elements for its ability to bond to itself to form
long chains and a myriad of structures. Of the approximately 11 million known
chemical compounds, about 10 million are organic. New advances in organic
chemistry have allowed the production of better polymers with specific proper-
ties, such as biodegradable plastics. The elucidation of new drug structures from
plants and the synthesis of improved pharmaceuticals is another area of great
interest. Organic chemists are also researching the reactions that occur in living
systems and understanding the molecular causes of disease.