Author Topic: Articles of Interest in Journals and Books  (Read 1496 times)

java

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Articles of Interest in Journals and Books
« on: October 24, 2009, 04:17:57 PM »
New  Strategies for the Hofmann Reaction
Dhananjay S. Rane 8z Man M. Sharma"
Journal of Chemical Technology & Biotechnology Volume 59 Issue 3, Pages 271 - 277, 2004


Abstract
Some new strategies, such as the use of hydrotropes, surfactants,
co-solvent, etc., were applied to the Hofmann reaction of fatty amides to obtain
isocyanates, amines and carbamates. Additionally, some industrially important
aromatic amines were synthesised.

Key words: Hofmann reaction, amides, synthesis of amines, isocyanates, carbamates,
alkylation of carbamates, use of surfactants, hydrotropes, co-solvent.


Note.......this might help get the amide into solution for better amine results
« Last Edit: March 09, 2010, 06:40:28 AM by java »
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java

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Re: Articles of Interest
« Reply #1 on: October 24, 2009, 06:03:16 PM »
The Action of Formaldehyde on Amines and Amino Acids'
BYH . T.C LARKEH, . B. GILLESPIAEN D S. 2. WEISSHAUS
Journal of the American Chemical Society 0002-7863, vol: 55 1933 p:4571


Summary
Simple aliphatic amines are smoothly methylated to the corresponding tertiary amines by warming in formic acid solution with formaldehyde.Dibenzylamine, under these conditions, is mainly converted into methyldibenzylamine, but at the same time yields some benzaldehyde and a more volatile base (probably dimethylbenzylamine).
Tetra-alkyl-diaminomethanes,o n warming with formic acid, are converted into equimolar quantities of the corresponding dialkylamine and methyldialkylamine. Hexamethylenetetramine reacts with warm formic
acid yielding mainly ammonia and trimethylamine, with smaller amounts of mono- and dimethylamines; only three-quarters of the methylene carbon reappears as methyl in the final mixture.
Only about two-thirds of the anticipated amount of carbon dioxide, calculated on the assumption that the formic acid is the sole hydrogen donor, is obtained in these reactions; apparently some of the formaldehyde also contributes hydrogen.
Amino acids react with formaldehyde in warm formic or acetic acid with detachment of some of the nitrogen in the form of volatile bases. Dimethyl derivatives were isolated from the reaction in formic acid with glycine, P-aminopropionic acid, a-aminoisobutyric acid and a-amino-aphenylbutyric acid. Other amino acids yielded breakdown and condensation of various degrees of complexity. Benzaldehyde was
isolated from a-aminophenylacetic acid, propiophenone from a-amino-aphenylbutyric acid, and a-(4-phenyl-2,3-diketopyrrolidyl)-/3-phenylpropionic acid from phenylalanine. Mechanisms by which these products may be formed are suggested.

« Last Edit: October 24, 2009, 06:09:11 PM by java »
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Sedit

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Re: Articles of Interest
« Reply #2 on: October 26, 2009, 06:32:34 PM »
 
Hydrobromination of Alkenes with PBr3/SiO2: a Simple and Efficient Regiospecific Preparation
of Alkyl Bromides
Antonio M. Sanseverino and Marcio C.S. de Mattos*

Quote
The reaction of several alkenes with 0.4 mol equiv. PBr3/SiO2 in dichloromethane at room
temperature gave the alkyl bromides with Markovnikov regiospecificity in 50 - 100% yield and
short reaction time. Isoprene at - 8 oC in these conditions gave 1-bromo-3-methyl-2-butene only
(54%).

Keywords: alkenes, bromides, electrophilic addition, regiospecificity, silica
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Sedit

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Re: Articles of Interest
« Reply #3 on: November 06, 2009, 06:25:02 PM »
Various demethylation reagents. I will edit and improve this post later on when I am on my own computer.

http://finechem.dlut.edu.cn/05icfm/article/review/Demethylating%20Reaction%20of%20Methyl%20Ethers.pdf
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jon

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Re: Articles of Interest
« Reply #4 on: November 06, 2009, 08:22:56 PM »
java so that article is saying fuckall about sec amines by deduction one can tweak it a little after much cursing and chemical analysis some sucess may be garnered no?

java

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Re: Articles of Interest
« Reply #5 on: November 17, 2009, 02:34:25 PM »
Amines and amides
Michael North
J. Chem. Soc., Perkin Trans. 1, 1998, pg. 2959

Contents
Covering: 1997
Previous review: Contemp. Org. Synth., 1997, 4, 326
1 Introduction, scope and coverage
2 Addition of nucleophiles to imines and related species
2.1 Methods giving achiral or racemic products
2.2 Methods utilizing a chiral imine or related species
2.3 Methods utilizing a chiral catalyst, ligand, or reagent
3 Other syntheses of amines and amides from imines and
their derivatives
4 Aziridine chemistry
4.1 Formation of aziridines
4.2 Formation of amines and amides by the ring opening
of aziridines or aziridinium ions
5 Synthesis of amines and amides using the Evans and
related auxiliaries
6 Synthesis of amines and amides using the Curtius and
related rearrangements
7 Synthesis of amines and amides by Michael additions
8 Transition metal mediated processes
9 Derivatization of amines and amides
10 New methods in peptide synthesis
11 Miscellaneous methods
12 References

-------------------------------------------------------------------

Amines and amides
Michael North
J. Chem. Soc., Perkin Trans. 1, 1999, 2209–2229 2209



Contents

Covering: 1998
Previous review: J. Chem. Soc., Perkin Trans. 1, 1998, 2959
1 Introduction, scope and coverage
2 Addition of nucleophiles to imines and related
species
2.1 Methods giving achiral or racemic products
2.2 Methods utilizing a chiral imine or related species
2.3 Methods utilizing a chiral catalyst, ligand, or reagent
3 Other syntheses of amines and amides from imines
and their derivatives
4 Aziridine chemistry
4.1 Formation of aziridines
4.2 Formation of amines and amides by the ring opening
of aziridines or aziridinium ions
5 Synthesis of amines and amides by Michael
additions
6 Transition metal mediated processes
7 Derivatization of amines and amides
8 New methods in peptide synthesis
9 Miscellaneous methods
10 References
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java

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Re: Articles of Interest
« Reply #6 on: November 17, 2009, 04:40:26 PM »
This may be of some help in getting some interesting articles.......java


http://www.toodoc.com/

.....Example put in search under PDF amines and amides....you get this ,

http://www.toodoc.com/search.php?t=pdf&q=amides+and+amides-++North

and if you want to find reduction of amides try this.....

http://www.toodoc.com/reduction-of-amides-pdf.html



......you get the ides and the articles are free.......java
« Last Edit: November 17, 2009, 04:45:57 PM by java »
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java

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Re: Articles of Interest
« Reply #7 on: November 19, 2009, 05:09:03 AM »
1-Phenylethylamines: a new series of illicit drugs?
L. A. King a, Corresponding Author Contact Information, A. J. Poortman-van der Meer b and H. Huizer
Forensic Science International, Volume 84, Issues 1-3, 17 January 1997, Pages 281-294


By chamula

Abstract
An important task for the forensic toxicologist and expert witness is the detection of the noxa in biological matrices. Because of this, the identification and quantification of residues of illegal drugs in human hair is still of growing interest. Utilizing the advantages of GC/MS/MS testing human hair is performed for most common drugs of abuse like heroin and other opioides, cocaine, cannabis and amphetamine derivatives. Analyzing hair specimens for substances that present a toxicological risk is another challenge. Several quality control parameters must be observed to avoid false positive or false negative results and to gain additional information. Blank sample, blank hair as well as the combined wash extracts are tested for the presence of the relevant compounds within every series. Careful evaluation of the findings can provide an approximate measure of the intensity of drug use in the majority of cases.

« Last Edit: November 19, 2009, 02:14:30 PM by java »
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Enkidu

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Re: Articles of Interest
« Reply #8 on: November 19, 2009, 07:38:58 AM »
^ which they aren't, iirc

java

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Re: Articles of Interest
« Reply #9 on: November 19, 2009, 02:17:03 PM »
java so that article is saying fuckall about sec amines by deduction one can tweak it a little after much cursing and chemical analysis some sucess may be garnered no?

.......experimenting is king,   so all synthesis are open for tweaking to serve our needs......java
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java

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Re: Articles of Interest
« Reply #10 on: November 19, 2009, 05:01:49 PM »
Application of the Evans Aziridination Procedure to 2-Substituted
Acrylates and Cinnamates : An Expedient Route to
¢x-Substituted ~- and ~-Amino Acids

Philippe Dauban and Robert H. Dodd
Tetrahedron Letters 39 (1998) 5739-5742

Abstract
Reaction of the title compounds with PhI=NSO2Ar (Ar = p-tolyl or p-nitrophenyl) its the
presence of catalytic copper (H) triflate in acetonitrile gave the corresponding 2 and~or 3-substituted
aziridine-2-carboxylates in generally good yields. The latter, on reaction with nucleophiles, gave o~-
substituted or- or [J-amino acids depending on the pattern of substitution on the aziridine ring.

Note- this may be the key to open up aziridines in a well known process
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java

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Re: Articles of Interest
« Reply #11 on: November 27, 2009, 07:09:47 PM »
STABILITY OF COCAINE IN AQUEOUS SOLUTION
John B. Murray, Hasan I. Al-Shora
Journal of Clinical Pharmacy and Therapeutics Volume 3, Issue 1 , Pages1 - 6,
1978


Abstract
The effect of pH on the rate of hydrolysis of cocaine was investigated. Ionic strength had a negligible effect while the concentrations of the various buffers had a significant effect on the rate of hydrolysis. The pH rate profile in buffer showed a minimum at 1.95. The energies of activation were determined to be 95.9, 107.3 and 97.9 kJ mol-1 respectively at pH 6.8, 5J0 and 2.2. The stability on storage of sterilized solutions of cocaine prepared by various methods and formulae was compared with the stability predicted from the results of the accelerated tests.
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Sedit

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Re: Articles of Interest
« Reply #12 on: December 04, 2009, 12:28:44 AM »
US Patent 4950833 - Process for the reductive dehalogenation of polyhaloaromatics


Reduction of organic halogenated compounds using a form of birch reduction where the proton donating ammonia is produced from the reaction of elemental alkali metals on an ammonia salt in a suitable solvent. I am curious as to wether this would work on benzylic alcohols as well.
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java

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Re: Articles of Interest
« Reply #13 on: January 03, 2010, 06:18:40 PM »
Synthetic Studies toward (+)-Lysergic Acid: Construction of the Tetracyclic Ergoline Skeleton
Tohru Inoue, Satoshi Yokoshima, and Tohru Fukuyama
Heterocycles
2009, Vol. 79, Issue 1, Pages 373-378
DOI: 10.3987/COM-08-S(D)42



Abstract
We have successfully constructed the tetracyclic skeleton of lysergic acid, which features an acylation at the C3 position of the indole as well as an
intramolecular Heck reaction. The optically active D ring unit could be derived  from L-pyroglutamic acid via a disrotatory electrocyclic reaction of a
dibromocyclopropane.
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java

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Re: Articles of Interest
« Reply #14 on: January 11, 2010, 03:27:14 PM »
A Palladium-Catalyzed Strategy for the Preparation of Indoles:  A Novel Entry into the Fischer Indole Synthesis
Seble Wagaw, Bryant H. Yang, and Stephen L. Buchwald
J. Am. Chem. Soc.
1998, 120 (26), pp 6621–6622
DOI: 10.1021/ja981045r


Summary
In summary, we have developed a method that provides an alternative source of substrates for Fischer indolizations. Central
to this strategy was the application of a palladium-catalyzed coupling procedure to prepare N-aryl benzophenone hydrazones,
and their use as general precursors to intermediates in the classical Fischer Indole Synthesis. We are currently applying this and
related methodologies toward the preparation of N-alkyl and N-aryl indoles, pyrroles, furans, and benzofurans, as well as the
synthesis of pharmaceutical targets and indole libraries
« Last Edit: January 11, 2010, 03:29:05 PM by java »
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Re: Articles of Interest
« Reply #15 on: January 25, 2010, 06:07:21 AM »
Novel one-pot synthesis of quaternary ammonium halides - new route to ionic liquids

New Journal of Chemistry
Jarmo Ropponen, Manu Lahtinen, Sara Busi, Maija Nissinen, Erkki Kolehmainen and Kari Rissanen
2004, 28, 1426 - 1430, DOI: 10.1039/b409062b

Abstract

Treatment of an amide with an alkyl or substituted alkyl halide
in the presence of a weak base in a one-pot reaction leads to
crystalline quaternary ammonium halides with reasonable chemical
yields; some of the compounds show low melting points
and a liquid range of over 50–100 C before decomposition.

java

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Re: Articles of Interest in Journals and Books
« Reply #16 on: March 09, 2010, 06:39:54 AM »
Reductions by the Alumino- and Borohydrides in Organic Synthesis (Second Edition)
Jacqueline Seyden-Penne


Forward
Although it may be difficult to imagine now, it was not that long ago that the basic
reduction of one organic functional group to another was a demanding proposition.
Choices of reagents were very limited, and reaction conditions were harsh. Enter the
alumino- and borohydrides. Lithium aluminohydride and sodium borohydride were
introduced by Schlesinger and Brown in 1953. Lithium aluminohydride was useful
because it reduced so many things, while the milder sodium borohydride effected
certain kinds of selective reductions in organic molecules. Soon the complexity of
molecules grew, and along with this complexity came the need for more reducing
agents with different properties and selectivities. So a few new alumino- and borohydrides
were introduced. But the spiral did not stop there. The complexity of
molecules grew rapidly, reductions became more and more demanding, and even
better and more selective reducing agents were introduced in response to this demand.
The response to the need for chiral reducing agents has recently sent this
spiral to new heights.
So it would appear that synthetic organic chemists should be happy, because for a
given kind a reduction—even a very demanding one—there is probably already an
alumino- or borohydride reducing agent and a set of reaction conditions that is up to
the task. But there is still unhappiness because finding the right combination from
the maze of catalogs, papers, and experimental procedures can itself be a daunting
task.
From out of this maze springs this book. Professor Jacqueline Seyden-Penne is
an acknowledged expert in the area. The book is a major update of the First Edition,
which was published in 1991 by VCH Publishers (a translation from the popular
first French edition). It includes the important developments that have occurred in
the intervening half-dozen years (notably in the area of asymmetric reductions).
Professor Seyden-Penne first describes the features of more than two dozen of the
most powerful and commonly used alumino- and borohydrides, and then goes on to
detail in individual chapters their reactions with important classes of organic molecules.
There is a strong emphasis on selectivity at every level (chemo-, regio-,
diastereo-, and enantioselection), and experimental practicality is also directly addressed.
Synoptic tables present much information at a glance, and extensive references
(about 1000) lead the reader back to the original papers and experimental
procedures.
The book is in effect a road atlas that allows the organic chemist to maneuver
rapidly through the maze of information on reductions of organic compounds by
alumino- and borohydrides to locate the desired goal. For anyone trying to navigate
in this area, this road atlas is indispensable.
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Goldmember

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Re: Articles of Interest in Journals and Books
« Reply #17 on: March 09, 2010, 06:50:36 AM »
This is interesting. Some may have seen it but I hadnt, although I have pondered its application on many occasions.

Nothing much new is described but it is pretty cool and the only reference Ive ever found explicitly pertaining to the titled product  (also MDPPA) rather than the amino ketone(yes I have searched high and low).

3,4 Dioxyalkylene phenyl) 2 Amino Alkanol
Ehrhart and Bockmuhl
9/16/1931


http://www.google.com/patents?id=H-1KAAAAEBAJ&printsec=abstract&zoom=4&source=gbs_overview_r&cad=0#v=onepage&q=&f=false

Written by the same guys who first patented methadone!

Enkidu

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Re: Articles of Interest in Journals and Books
« Reply #18 on: March 12, 2010, 09:26:26 PM »
The Dakin–West reaction
G. L. Buchanan
Chem. Soc. Rev., 1988, 17, 91 - 109, DOI: 10.1039/CS9881700091

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Future Synthetic Drugs of Abuse
« Reply #19 on: March 18, 2010, 02:03:13 AM »
Future Synthetic Drugs of Abuse
Donald A. Cooper
Proceedings of the International Symposium on the Forensic Aspects of Controlled Substances

This paper from 1988 is still a valuable map for ambitious clandestine chemists today. So many of the discussed compounds have rarely or never been prepared clandestinely! The paper should be well-known to many here from the old Rhodium site, but Rhodium only provided an HTML transcript. I think this scan of the original looks nicer, plus it has the tables and figures that were missing from the transcription.