A heap more journals related to; safrole/eugenol/allylbenzes

nubee · Master Archiver

these journals turned up from search results for safrole synthesis and some from eugenol,cinnnamaldehyde, and allylbenzyenes, plus a few other random relatives

some may not be usefull at all, but perhaps would make usefull learning references for new-bee's...

sorry for issue with descriptions as often OCR is buggy and i was in hurry.

backups will be held, as rapidshare deletes after 30 days of inactivity so requests can be made, but it'd be good for atleast a few people to get copies of them.

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

Journal of Molecular Catatysis, 36 (1986) 349 - 357

INFLUENCE OF VARIOUS PARAMETERS ON THE SELECTIVITY OF
THE PRODUCTION OF ALDEHYDES STARTING FROM ALKENES
ISSUED FROM THE BIOMASS AND USING THE CATALYST
PRECURSORS ~~(~SR~~(CO)~(PA~~*

Abstract: The effects of solvent, ligand L and R group for the catalyst precursor
[Rh~(~-SR)~(CO~*L*] and of the ally1 benzene (estragole, eugenol, eugenol
methyl ether and safrole) on the yields, rates and ~~o~l~ctivi~es of the
substrate conversion into aldehydes have been examined. The reactions can
be performed in 90 min at 80 “C and 5 bars of a CO/H, mixture to give up to
95% of the expected aldehydes with complete selectivity. Polar but noncoordinating
solvents are preferable.

http://rapidshare.de/files/1345789/05032011171214059.pdf.html

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

http://rapidshare.de/files/1345841/05032011191114271.pdf.html

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

Journal of Molecular Catalysis, 58 (1990) 387-392

CARBON MONOXIDE AS A BUILDING BLOCK FOR ORGANIC
SYNTRESIS
PART I. HIGHLY BEGIOSELECTIVE ALKOXYCARBONYLATION
OF ALLYLBENZENE CATALYZED BY PALLADIUM COMPLEXES

Summary
The various parameters governing the alkoxycarbonylation of 3-
phenylpropene were investigated in order to select an efficient catalytic
system for the conversion of various naturally-occurring allylbenzenes into
the corresponding esters. The complex PdC12(PPh&, in the presence of a
slight excess of phosphine and SnC12.2H,0 catalyzed this reaction at 4 MPa,
with a good selectivity and a regioselectivity in linear ester as high as 95%.
Several diphosphine ligands were conveniently used, and in many cases the
regioselectivity was controlled by the reaction conditions.

http://rapidshare.de/files/1345855/05032011203714473.pdf.html

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

Journal of Molecular Catalysis, 78 (1993) 351-366

Carbon monoxide as a building block in organic synthesis
Part II. One-step synthesis of esters by alkoxycarbonylation
of naturally occurring allylbenzenes, propenylbenzenes and
monoterpenes

Abstract
Various allylbenzenes (estragole, eugenol, eugenol methyl ether, safrole), propenylbenzenes
(the iso compounds) and monoterpenes (limonene, isopulegol, isopulegyl acetate) were
converted into the corresponding esters by alkoxycarbonylation at 4 MPa and 100 “C.
Two palladium systems were used to catalyze this reaction: [PdCl,(PPh,),] and
[PdCla(PPh,),]/SnCla .ZHaO when larger amounts of linear ester are expected. This reaction
was shown to be highly selective, since only the terminal carbon-carbon double bond
was transformed. Isopulegol gave rise to a cyclocarbonylation reaction leading to the
corresponding Nactone.

http://rapidshare.de/files/1345876/05032011193014302.pdf.html

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

Tetrahedron report number 631

Oxidative degradation of benzene rings

1. Introduction
Since the late 19th century, benzene ring degradation has
been used to help elucidate and identify the structure of
unknown compounds, like morphine,1,2 for example.
Although in some early cases the structures of the products
were not conclusive, more recent studies have alleviated
initial problems, allowing broader application. It is this
broader application which the authors wish to bring to the
attention of the chemical community.
In particular, this review is concerned with the formation of
ring-cleaved products such as carboxylic acids, lactones,
muconic acids and their respective derivatives, thereby
expanding the utility of benzenoid synthons in organic
synthesis.

http://rapidshare.de/files/1345926/05032011210114519.pdf.html

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

http://rapidshare.de/files/1345955/05032011220714629.pdf.html

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

Tetrahedron 60 (2004) 5481–5485

Synthesis of methylenedioxy-bearing
1-aryl-3-carboxylisoquinolines using a modified
Ritter reaction procedure

Abstract—This paper describes original approaches aimed at the preparation of electron-rich 1-aryl-3-carboxylisoquinolines. Our first
attempt led to an efficient preparation of 1-hydroxyisoquinoline-3-carboxylic acid methyl ester starting from bromophthalide via a
rearrangement of 2-acetylamino-2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-malonic acid dimethyl ester. However, as its eventual application
to the synthesis of methylenedioxy-bearing substrates seemed rather long, a second approach involving an extension of the Ritter reaction to
safrole was devised. We thus report that, under proper experimental settings, the use of 54% tetrafluoroboric acid in ether enables a
Ritter reaction between safrole and 3,4,5-trimethoxybenzonitrile yielding 17% of 7-methyl-5-(3,4,5-trimethoxyphenyl)-7,8-dihydro-
[1,3]dioxolo[4,5-g]isoquinoline. This acidic reagent avoids the extensive decomposition seen when using the classical Ritter reaction
conditions (i.e.: concentrated sulfuric acid). Further chemical transformations of this methyl-bearing dihydroisoquinoline led to the
methylenedioxy-bearing 1-aryl-3-carboxylisoquinoline. These derivatives are related to the peripheral benzodiazepine receptor ligand PK
11195 as well as falcipain-2 inhibitors and other potential antitumor agents.

http://rapidshare.de/files/1345771/05032011251114908.pdf.html

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

Temahedmn Lams, Vol. 35. No. 21. pp. 3531-3538, 1994

Addition of Diethyl T~~h~o~methyIph~phonate to Olefins
Catalysed by Copper Complexes

Abstract: Die&y1 trichl~methyl phospbonate is added on olefins by non-chain catalytic reactions catalysed ;by
ccpper amine complexes.

http://rapidshare.de/files/1345972/05032011254914959.pdf.html

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

Tetrahedron Letters,Vol.29,No.7,pp 765-768,1988

ELECTROCATALYTIC OXIDATION OF OLEFINES AND KETONES
BASED ON A Ru I"= O/RuII- H20 SYSTEM.

Abstract: An electrocatalytic procedure is described for the oxidation ofcyclohexene,
safrole, isosafrole, isophorone, deoxybenxoin and acetophenone using the Ru
IV
oxidant
[RI?" (trpy)(bpy)Ol'+. The relative reactivities of the substrates are presented.

http://rapidshare.de/files/1345991/05032011291215244.pdf.html

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

Tetrahedron Letters No.10, pp. 1241-1245, 1968.

A NEW APPROACH TO ISOQuINOLINES.1

A major source of 3,4-dihydroisoquinolines is the Bischler-Napieralski
reaction, which involves the cyclization of aryl-ethyl amides by dehydrating
agents 2 . Buu-Hoi and co-workers,in their study of d,d-dimethyl -/j-arylethylamines
found that the corresponding N-acetyl and N-benzoyl derivatives
could not be cyclodehydrated to 3,3-dimethyl-3,4-dihydroisoquinoline~~.
Buu-Hoi attributed this failure to steric hindrance, while Prajsnar 3 explained
it as the result of a reverse Ritter reaction. Based on our studies
of nitrilium ion intermediates as a method of introducj?g nitrogen functions
into organic molecules3, we have developed a method of synthesis of 3,4-
dihydroisoquinolines from olefins. This has allowed us to synthesize 3,3-
disubstituted-3,4-dihydroisoquinolines, which can not be obtained from the
Bischler-Napieralski reaction.
An additional advantage of our method is the functionalization of the
3' position with a halogen substitutent, which should be useful in alkaloid
synthesis.

http://rapidshare.de/files/1346003/05032011293115258.pdf.html

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

.Iournal of ~rga~ometallic Chemistp, 319 (1987) 113-117

ISOMERIZATION OF OLEFINS CATALYSED
BY A CoCl,/Ph,P/NaBH, SYSTEM

Summary
The catalyst generated in situ using CoCl,/PhsP/NaBH, in l/3/1 ratio in
THF at -lO*C isomerizes 1-decene into predo~nantly c&Z-decene or trans-Z
decene. Ally1 benzene and safroie have been converted into the corresponding
fi-methylstyrenes. The catalyst also isomerizes cis,cis-1,Scyclooctadiene to cis,cis-
1,3-cyclooctadiene.

http://rapidshare.de/files/1346018/05032011305715436.pdf.html

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

Terrahcdron Vol 26. pp 4005 10 4018

ASPECTS OF ARYNE CHEMISTRY- II’
THE REACTION BETWEEN ISOSAFROLE AND DIAZOTISED
ANTHRANILIC ACID UNDER DIFFERENT CONDITIONS*

Abe&act-- The main products derived from the interaction of isosafrole with either benxenediazonium-2-
carboxylate, or with anthranilic acid and amyl nitrite, are the phenanthrene derivatives expected from a
Diels-Alder addition involving benzyne as an intermediate. With benxenediaxonium-2carboxylate
hydrochloride and isosafrole, however, the chief product is rrans-3-(3’,4’-methylenedioxyphenyl)4methyl-
3+dihydroisocoumarin. The reasons for this difference in behaviour are discussed.

http://rapidshare.de/files/1346029/05032011323115563.pdf.html

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

http://rapidshare.de/files/1346036/05032011330415642.pdf.html

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

Il Farmaco 57 (2002) 999/1007

Synthesis and pharmacological evaluation of novel antinociceptive Nsubstituted-
phenylimidazolyl-4-acylhydrazone derivatives

Abstract
This paper describes recent results of design, synthesis and pharmacological evaluation of new N-heterocyclic functionalized Nacylhydrazone
compounds (NAH), belonging to the N-substituted-phenylimidazolyl-4-acylhydrazone class (3a/o). These
compounds were planned by applying the molecular hybridization strategy to propose the structural modifications on the
previously described functionalized 2-methyl-imidazolyl-3-acylhydrazone class (2), which presented an important analgesic profile.
This new series (3) was synthesized in order to investigate the possible pharmacophoric contribution of the N-heteroaromatic ring
and N-acylhydrazone moieties to the analgesic activity. Compounds 3g and 3n are the most potent analgesic agents from this series,
at the screening dose of 100 mg/kg p.o. and compounds 3e, 3j and 3o presented the best antiinflammatory properties at the same
screening concentration.

http://rapidshare.de/files/1346046/05032011334015685.pdf.html

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

Tetrahedron Letters, Vo1.27, No.5, pp 645-648, 1986

HORNER-WITTIG REACTIONS USING DIBENXOPHOSPHOLE OXIDES:
STEREDCHERICALLY CONTROLLED REDUCTION OF KETONES

Reduction of ketones having an a-dibenzophosphole-5-oxide gKOUp with NaBH4, LSelectride,
or Superhydride gives threo Horner-Wittig intermediates and hence
E-alkenes, while NaBH4/CeC13 gives erythro intermediates and hence Z-alkenes.

http://rapidshare.de/files/1346057/05032011335515699.pdf.html

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

Tenakdron Vol. 42, No. 20. pp. 5515 to 5522 1986

ORGANOBORANES FOR SYNTHESIS, 4. OXIDATION OF ORGANOBORANES WITH PYRIDINIUM
CHLOROCHROMRTE. A DIRECT SYNTHESIS OF ALDEHYDES FROH TERMINAL ALKENES
VIA HYDROBORATION

Abstract. The oxidation of trialkylboranes containing primary alkyl groups
midinium chlorochromate (PCC) in methylene chloride provides the corresponding
aldehydes in good yields. The stofchiometry for the oxidation of
alcohols, borate esters and trialkylboranes with PCC has been examined. In
vfew of the poor regioselectivity (only 94% primary alkyl groups) and functional
group tolerance observed in the hydroboration with borane (BH3.THF or
BH3.SMe2). a more selective hydroboratfng agent, bis(J-methyl-2-butyl)borane
(disiamylborane). was utilized for the preparation of aldehydes from terminal
alkenes. However, the formation of 3-methyl-2-butanone as a by-product, and
the requirement of six moles of PCC per mole of aldehyde are major disadvantages
in this method. This difficulty was circumvented by employing monochloroborane-
dimethyl sulfide for hydroboration. This reagent exhibits high
regioselectivfty (> 99% primary alkyl groups) in the hydroboration of terminal
alkenes. Oxidation of the resulting dialkylchloroborane followfng hydrolysis
affords the desired aldehydes in satisfactory yields. Consequently,
the hydroboration of terminal alkenes, followed by PCC oxidation, represents
a direct convenient method for the transformation of alkenes into the corresponding
aldehydes.

http://rapidshare.de/files/1346073/05032011341115725.pdf.html

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

Organic Geochemistry 30 (1999) 607±621

Tetramethylammonium hydroxide (TMAH)
thermochemolysis: proposed mechanisms based upon the
application of 13C-labeled TMAH to a synthetic model lignin
dimer

Abstract
The mechanism by which heated tetramethylammonium hydroxide (TMAH) degrades the lignin biopolymer was
investigated by the novel application of 13C-labeled TMAH (13C-TMAH) in the thermochemolysis of a synthetic
model guaiacyl lignin dimer. GC-MS analysis of the products showed labeling patterns consistent with a base-
catalyzed intramolecular displacement of the b-phenoxy group and the formation of two intermediate guaiacyl
propane epoxides, a g-hydroxy-a,b-epoxide and an a-hydroxy-b,g-epoxide. Methoxide then functions as a
nucleophile to open the epoxide ring. These results substantiate the base-catalyzed reactions previously postulated
by Gierer (1970) to explain alkali wood pulping and also explain the facile formation and distribution of lignin
derivatives obtained in the TMAH thermochemolysis of natural samples. The absence of substantial numbers of
bonds involving propyl-aryl ether linkages with adjacent hydroxyl groups is the limiting factor in the complete
decomposition of lignin by TMAH thermochemolysis, as propyl-aryl ether linkages without adjacent hydroxyl
groups cannot react via this mechanism. This helps to explain why materials such as highly degraded lignin residues,
with signi®cant side chain alteration and type III kerogens above the rank of lignite, where aliphatic-aryl ether
linkages are thought to be insigni®cant, are reported to give low yields of TMAH thermochemolysis
products. # 1999 Elsevier Science Ltd. All rights reserved.

http://rapidshare.de/files/1346079/05032011383016253.pdf.html

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

PALLADIUM-CATALYZED ADDITION REACTION OF
OLEFINS, CARBON TETRACHLORIDE
AND
CARBON MONOXIDE IN ALCOHOLS TO GIVE
2-ALKYL_4,4+TRICHLOROBUTANOATES

Abatraet-Pd(OAc), combined with PPh, is a good catalyst for the addition reaction of CCl, and CO to
olefins in ethanol to afford ethyl 2-alky14,4&trichlorobutanoates. The esters were obtained in satisfactory
yields when the reaction was carried out at 50” in the presence of K&O, under CO pressure.

http://rapidshare.de/files/1346085/05032011393516367.pdf.html

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

Catalysis Today 66 (2001) 381–387

Kinetics of cinnamaldehyde hydrogenation–concentration
dependent selectivity

Abstract
For the isothermal hydrogenation of cinnamaldehyde over Pt/C/monolithic catalysts three kinetic models have been evaluated,
each model based on different sets of assumptions. A single-site and a two-site model with the surface reactions as
rate-controlling steps were unable to describe the experimental data satisfactorily, while a single-site model with adsorption,
surface reactions, and desorption all rate controlling could describe the experimental data adequately. This model includes
apparent direct reaction steps from reactant to various end-products, due to the competition between desorption and subsequent
conversion of intermediates at the catalyst surface. The selectivity to the unsaturated alcohol increases with increasing
reactant concentration, which is ascribed to a change in adsorption mode, possibly due to some assembling phenomena of the
reactant at the catalyst surface. © 2001 Elsevier Science B.V. All rights reserved.

http://rapidshare.de/files/1346121/05032011423216624.pdf.html

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

http://rapidshare.de/files/1346086/05032011382416247.pdf.html

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

Applied Catalysis, 78 (1991) 165-197

Hydrogenation activity and selectivity of cobalt borides

Ah&act
Hydrogenation of monofunctional (olefinic and carbonyl) and bifunctional (a, jkmaaturated aldehyde)
compounds have been studied over cobalt borides. The cobalt boridea P-1Co and P-2WCo were
prepared by reducing cobalt acetate with sodium borohydride in aqueous and 50% etbanolic media,
respectively. P-1Co is more active than P-2WcO for hydrogenation of olefinic groups, whereas P-1Co is
less active for carbonyl groups. Chromium and molybdenum effectively promote P-1Co and P-2WCo in
carbonyl group reduction, but chromium depresses P-1Co and P-2WcO on olefinic group reduction. P-
1Co and P-2WCo can selectively reduce benzene to cyclohexene and (Y, /%maaturated aldehyde to unsaturated
alcohol, reactions that are difficult on other heterogeneous catalyets.

http://rapidshare.de/files/1346151/05032011465917005.pdf.html

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

http://rapidshare.de/files/1346170/05032011483517221.pdf.html

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

Terrakdmn Vol 41, No. 23, pp. 5645 to S6S1, 1985

PALLADIUM-CATALYSED OXIDATION OF ALCOHOLS
WITH CARBON TETRACHLORIDE, FORMATION OF 4,4,4-
TRICHLORO KETONES FROM ALLYLIC ALCOHOLS AND
CARBON TETRACHLORIDE OR
BROMOTRICHLOROMETHANE, AND CONVERSION OF
HALOHYDRINS TO KETONES

Ah&act-Pd salts catalyse oxidation of alcohols with Ccl, in the presence of K&O,. Primary alcohols are
oxidised to esters, and secondary alcohols to ketones. Ccl., is converted to CHCIJ. The reaction of allylic
alcohols bearing a terminal olefinic bond with CCl, or BrCCl, in the presence of palladium catalyst at 110”
alfords 4,4&trichloro ketones. At W, simple adducts of CCl,, or BrCCl, having a halohydrin structure are
obtained, which are converted to the corresponding trichloro ketones by the catalysis of palladium. Various
halohydrins are converted to ketones by Pd catalysis.

http://rapidshare.de/files/1346182/05032011484317231.pdf.html

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

http://rapidshare.de/files/1346257/05032011490017253.pdf.html

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

Journal of Organometallic Chemistry, 285 (1985) 231-252

DIRECT CONVERSION OF ALRENES INTO METI-IYLSURSTITUTED
CYCLOPROPANES USING AN ORGANOIRON ETIIYLID ENE TRANSFER
REAGENT *

Summary:

(q5-C5H5)(C0)2FeCH(CH3)SPh ( Cool

serves as a quite useful reagent for the
transfer of ethylidene groups to alkenes to give methyl-substituted cyclopropanes in
good yields. The reaction is accomplished by allowing 8 to react with an alkylating
agent such as trimethyloxonium tetrafluoroborate or methyl fluorosulfonate in the
presence of the alkene substrate. The active ethylidene transfer reagent is apparently
a sulfonium salt which is too reactive to be isolated under normal conditions. In all
cases, cyclopropanes are obtained stereospecifically with respect to the configuration
of the starting alkenes, and with certain classes of substrates such as cis-disubstituted
alkenes, the reaction also occurs with very high syn-stereoselectivity.

http://rapidshare.de/files/1346271/05032011524317584.pdf.html

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

T~rrobrdron Vol. 27. pp. 620142&S.

A RATIONALIZATION OF NITROSOARENE-OLEFIN
REACTIONS

Aladract-Previously described reaction products of nitrosoarenes with oldins can be rationalized on the
basis of two types of interaction dependent on whether the oldin contains an allylic H atom or not In the
former case, a reactive N-alkenyl-N-arylhydroxylamine is formed via an ‘ene’ addition reaction. This
hydroxylamine may either: (i) attack the nitrosoarene to form an azoxyarene and a nitrone: (ii) decompose
thermally to an N-alkenylanilioe and a nitrone: (iii) undergo dehydration to an anil. The balance between
these competing reactions and hena the ultimate reaction products is shown to be dependent on the nature
of the substituent on the nitrosoarene.

http://rapidshare.de/files/1346264/05032012011018627.pdf.html

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

SYNTHESIS OF l-[2’,5’-DIMETHOXY-4’-(P-FLUOROETHYL)PHENYL]-2-
AMINOPROPANE: STUDIES RELATED TO l*F-LABELED
SEROTONIN RECEPTOR LIGANDS

John M. Gerdes”, Chester A. Mathis and Alexander T. Shulgin
Donner Laboratory, Lawrence Berkeley Laboratory
University of California, Berkeley CA 94720

Abstract: Synthesis of the titled 2,5-dimethoxy-4-fluoroalkylamphetamine is reported. The highly functionalized
aromatic nucleus of the key fluorination precursor was utimately derived from a low temperature aromatic
halogen-lithium exchange reaction followed by alkylation of the resultant anion with ethylene oxide.

http://rapidshare.de/files/1346309/05032012470822764.pdf.html

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

Synthesis of allylbenzenes

by cross-coupling of allyl bromide with arylboronic acids using
a palladium chloride and tetraphenylphosphonium bromide
intercalated clay catalyst

Summary
A facile route for the synthesis of allylbenzenes is described from
easily accessible allyl bromide and arylboronic acids using a new
reusable catalyst system, palladium chloride and tetraphenylphosphonium
bromide intercalated clay.

http://rapidshare.de/files/1346302/displayarticlefree.pdf.html

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

http://rapidshare.de/files/1346320/05032011505717432.pdf.html

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

Synthesis of Isoquinolines and Pyridines by the Palladium/
Copper-Catalyzed Coupling and Cyclization of Terminal
Acetylenes and Unsaturated Imines: The Total Synthesis of
Decumbenine B

Monosubstituted isoquinolines and pyridines have been prepared in good to excellent yields via
coupling of terminal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-
alkenals in the presence of a palladium catalyst and subsequent copper-catalyzed cyclization of
the intermediate iminoalkynes. In addition, isoquinoline heterocycles have been prepared in
excellent yields via copper-catalyzed cyclization of iminoalkynes. The choice of cyclization conditions
is dependent upon the nature of the terminal acetylene that is employed, as only aryl and alkenyl
acetylenes cyclize under the palladium-catalyzed reaction conditions that have been developed.
However, aryl-, vinylic-, and alkyl-substituted acetylenes undergo palladium-catalyzed coupling
and subsequent copper-catalyzed cyclization in excellent yields. The total synthesis of the
isoquinoline natural product decumbenine B has been accomplished in seven steps and 20% overall
yield by employing this palladium-catalyzed coupling and cyclization methodology.

http://rapidshare.de/files/1346909/J._Org._Chem._2002__67__86-94.pdf.html

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

Eur. J. Org. Chem. 2005, 475–479

Recent Developments in Catalytic, Asymmetric α-Halogenation: A New
Frontier in Asymmetric Catalysis

The development of milder and more sophisticated halogenating
reagents that offer significantly greater chemoselectivity
and stereocontrol than diatomic halides has been critical
to the realization of asymmetric α-halogenation. Within
the past few years several groups have reported catalytic,
enantioselective methods for α-halogenation achieved by utilizing
the catalytic generation of either enolates (zwitterionic
or metal-based charge delocalized) or enamines. Most im-

portantly, this recent work has greatly enhanced the synthetic
utility of organic halogenations and, in doing so,
opened up a promising new frontier in organic synthesis.
This microreview presents recent advances in the area of
catalytic, asymmetric α-halogenations of carbonyl compounds

http://rapidshare.de/files/1346626/Eur._J._Org._Chem._2005__475_479.pdf.html
---------------------------------

Laughing