- Intermolecular Palladium-Catalyzed Oxidative Fluorocarbonylation of Unactivated Alkenes: Efficient Access to β-Fluorocarboxylic Esters
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A novel palladium-catalyzed intermolecular oxidative fluorocarbonylation of alkenes has been developed, in which employment of a cooperative process with electrophilic ArIF2-meidated alkenes activation and palladium-catalyzed carbonylation is c
- Qi, Xiaoxu,Yu, Feng,Chen, Pinhong,Liu, Guosheng
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- Fine-tuning latent fingerprint detection on paper using 1,2-indanedione bi-functional reagents
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In order to address the need for consistency and generality in chemical methods developed for detection of latent fingerprints on paper substrates, a practical protocol was developed using 1,2-indanedione-based bi-functional reagents. A series of novel bi
- Lee, Jisun,Joullié, Madeleine M.
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- ISOMERIZATION REACTIONS OF LITHIUM N-BUTYL-4-PENTENYLAMIDE
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Lithium N-butyl-4-pentenylamide (1) in tetrahydrofuran at 22 deg C rearranged smoothly to give a mixture (after protonation) of 1-butyl-2-methylpyrrolidine, formed by an unusual cyclization process, and cis- and trans-N-butyl-pentenylamine; in the presence of 2.0 molar equiv of hexamethylphosphoramide, the total rate of isomerization was accelerated by a factor of 2.5.
- Newcomb, Martin,Burchill, Michael T.
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- Metal-free Photochemical Atom Transfer Radical Addition (ATRA) of BrCCl3 to Alkenes
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A simple, photochemical, and metal-free protocol for the atom transfer radical addition (ATRA) of bromotrichloromethane onto various alkenes is described. Among a range of organic molecules, phenylglyoxylic acid proved to be the most suitable photoinitiator to promote a sustainable process for the addition of bromotrichloromethane to olefins. This photochemical atom transfer radical protocol can be expanded into a wide substrate scope of aliphatic olefins bearing various functional groups, leading to the corresponding products in good to excellent yields.
- Nikitas, Nikolaos F.,Voutyritsa, Errika,Gkizis, Petros L.,Kokotos, Christoforos G.
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supporting information
p. 96 - 101
(2021/01/04)
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- Highly Regioselective Copper-Catalyzed Transfer Hydrodeuteration of Unactivated Terminal Alkenes
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Catalytic transfer hydrodeuteration of unactivated alkenes is challenging because of the requirement that chemically similar hydrogen and deuterium undergo selective insertion across a π-bond. We now report a highly regioselective catalytic transfer hydro
- Clark, Joseph R.,Reyes, Albert,Torres, Emanuel Rivera,Vang, Zoua Pa
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supporting information
(2022/01/06)
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- Synthesis and characterization of light-fluorous NHC-ligands and their palladium complexes
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Light-fluorous ponytails containing perfluoro-n-propyl, perfluoro-n-butyl and perfluoro-t-butoxy groups were used to synthesize light-fluorous α-olefins, branched dialkyl iodides, alkyl triflates, alkyl imidazoles, and dialkyl imidazolium salts. The latte
- Horváth, István T.,Lo, Angel S. W.,Yiu, Ken S. M.
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- Mechanistically Guided Design of Ligands That Significantly Improve the Efficiency of CuH-Catalyzed Hydroamination Reactions
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Using a mechanically guided ligand design approach, a new ligand (SEGFAST) for the CuH-catalyzed hydroamination reaction of unactivated terminal olefins has been developed, providing a 62-fold rate increase over reactions compared to DTBM-SEGPHOS, the previous optimal ligand. Combining the respective strengths of computational chemistry and experimental kinetic measurements, we were able to quickly identify potential modifications that lead to more effective ligands, thus avoiding synthesizing and testing a large library of ligands. By optimizing the combination of attractive, noncovalent ligand-substrate interactions and the stability of the catalyst under the reaction conditions, we were able to identify a finely tuned hybrid ligand that greatly enables accelerated hydrocupration rates with unactivated alkenes. Moreover, a modular and robust synthetic sequence was devised, which allowed for the practical, gram-scale synthesis of these novel hybrid ligand structures.
- Thomas, Andy A.,Speck, Klaus,Kevlishvili, Ilia,Lu, Zhaohong,Liu, Peng,Buchwald, Stephen L.
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supporting information
p. 13976 - 13984
(2018/10/25)
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- Fluorofunctionalization of C=C Bonds with Selectfluor: Synthesis of β-Fluoropiperazines through a Substrate-Guided Reactivity Switch
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The halofunctionalization of alkene substrates remains an essential tool for synthetic chemists. Herein, we report regioselective ammoniofluorination of unactivated alkenes through photochemical means. A one-pot transformation of the ammonium fluoride products into pharmaceutically relevant β-fluoropiperazines is highlighted. Furthermore, a substrate-guided reactivity switch is observed: certain alkenes are shown to react with the same fluorinating reagent to instead give the less-substituted fluoride. We hope that the ammoniofluorination reaction will be of utility in the area of medicinal chemistry, where nitrogen and fluorine are among the most important heteroatoms.
- Capilato, Joseph N.,Bume, Desta Doro,Lee, Wei Hao,Hoffenberg, Louis E. S.,Jokhai, Rayyan Trebonias,Lectka, Thomas
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p. 14234 - 14244
(2019/01/03)
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- Exploring physicochemical space: Via a bioisostere of the trifluoromethyl and ethyl groups (BITE): Attenuating lipophilicity in fluorinated analogues of Gilenya for multiple sclerosis
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The direct, catalytic vicinal difluorination of terminal alkenes via an I(i)/I(iii) manifold was exploited to install a chiral, hybrid bioisostere of the CF3 and Et groups (BITE) in Gilenya; the first orally available drug for the clinical management of Multiple Sclerosis (MS). This subtle fluorination pattern allows lipophilicity (logD) to be tempered compared to the corresponding CF3 and Et derivatives (CH2CH3 > CH2CF3 > CHFCH2F).
- Erdeljac, Nathalie,Kehr, Gerald,Ahlqvist, Marie,Knerr, Laurent,Gilmour, Ryan
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supporting information
p. 12002 - 12005
(2018/11/21)
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- Piperazine derivatives and their use as therapeutic agents
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Compounds for treating an SCD-mediated disease or condition in a mammal, preferably a human, are disclosed, wherein the compounds are of formula (I): where x y, W, V, R 2 , R 3 , R 4 , R 5 , R 6 , R 6a , R 7 , R 7a , R 8 , R 8a , R 9 and R 9a are defined herein. Pharmaceutical compositions comprising the compounds of formula (I) are also disclosed.
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Paragraph 0125
(2016/03/19)
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- Copper-Catalyzed Three-Component Azidotrifluoromethylation/Difunctionalization of Alkenes
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A novel three-component strategy for the azidotrifluoromethylation of alkenes has been presented here. The reaction proceeded smoothly under gentle temperature and gave the bifunctional olefins in high yields. Furthermore, 1,3-dipolar reactions between az
- Yang, Mingbo,Wang, Wenlu,Liu, Yin,Feng, Lijie,Ju, Xuexia
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supporting information
p. 833 - 837
(2015/11/03)
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- NHC-copper hydrides as chemoselective reducing agents: Catalytic reduction of alkynes, alkyl triflates, and alkyl halides
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The NHC-copper-catalyzed Z-selective semi-reduction of terminal and internal alkynes, as well as the NHC-copper-catalyzed reduction of primary alkyl triflates and primary and secondary alkyl iodides and bromides are described. The high chemoselectivity demonstrated in these examples illustrates the mild nature of copper hydride complexes as reducing agents, which have applications in synthetic chemistry beyond their traditional role in the reduction of activated alkenes and carbonyl compounds.
- Cox, Nick,Dang, Hester,Whittaker, Aaron M.,Lalic, Gojko
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supporting information
p. 4219 - 4231
(2014/06/09)
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- An efficient regioselective hydrodifluoromethylation of unactivated alkenes with TMSCF2CO2Et at ambient temperature
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A mild, versatile and efficient method for the regioselective hydrodifluoromethylation of unactivated alkenes has been developed. This Ag-mediated Csp3-CF2 bond forming reaction provides easy access to a variety of vicinal α-difluoro
- Ma, Guobin,Wan, Wen,Li, Jialiang,Hu, Qingyang,Jiang, Haizhen,Zhu, Shizheng,Wang, Jing,Hao, Jian
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supporting information
p. 9749 - 9752
(2014/08/18)
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- Copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes
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A novel and highly practical reaction for the copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes is presented here. This methodology provides a general and straightforward way to synthesize a variety of useful CF3-containing nitriles, which can be used for further preparation of pharmaceutically and agrochemically important compounds in synthetic organic chemistry.
- He, Yu-Tao,Li, Lian-Hua,Yang, Yan-Fang,Zhou, Zhao-Zhao,Hua, Hui-Liang,Liu, Xue-Yuan,Liang, Yong-Min
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supporting information
p. 270 - 273
(2014/01/23)
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- Monophasic catalytic system for the selective semireduction of alkynes
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A highly efficient semireduction of alkynes has been developed. Using 0.5-2 mol % of a copper catalyst, semireduction can be accomplished with a wide range of substrates, including both internal and terminal alkynes without over-reduction. The new method has excellent chemoselectivity, and the semireduction can be accomplished even in the presence of nitro and aryl iodo groups. Finally, commercial availability of a catalyst precursor adds to the appeal of the new catalytic system.
- Whittaker, Aaron M,Lalic, Gojko
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supporting information
p. 1112 - 1115
(2013/04/10)
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- Simplifying nickel(0) catalysis: An air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes
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The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy2Ph)2Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.
- Standley, Eric A.,Jamison, Timothy F.
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supporting information
p. 1585 - 1592
(2013/03/14)
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- Copper-catalyzed highly selective semihydrogenation of non-polar carbon-carbon multiple bonds using a silane and an alcohol
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A copper catalyst bearing a suitable Xantphos derivative or NHC ligand was found to be highly efficient for the selective semihydrogenation of non-polar unsaturated compounds using a mixture of a silane and an alcohol as reducing agent. The catalytic system was useful for the selective semihydrogenation of internal alkynes to (Z)-alkenes with suppression of overreduction to the corresponding alkanes. Furthermore, semihydrogenations of terminal alkyne, 1,2-diene, 1,3-diene, 1,3-enyne and 1,3-diyne systems were also achieved selectively. Copyright
- Semba, Kazuhiko,Fujihara, Tetsuaki,Xu, Tinghua,Terao, Jun,Tsuji, Yasushi
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supporting information; experimental part
p. 1542 - 1550
(2012/08/08)
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- Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles
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The Pd(0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated SN2-type stereoinvertive oxidative addition of unactivated primary and secondary alkyl tosylates.
- Stokes, Benjamin J.,Opra, Susanne M.,Sigman, Matthew S.
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supporting information; experimental part
p. 11408 - 11411
(2012/09/05)
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- Preparation of carbohydrate arrays by using Diels-Alder reactions with inverse electron demand
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Carbohydrate microarrays are an emerging tool for the high-throughput screening of carbohydrate-protein interactions that represent the basis of many biologically and medicinally relevant processes. The crucial step in the preparation of carbohydrate arrays is the attachment of carbohydrate probes to the surface. We examined the Diels-Alder reaction with inverse-electron-demand (DARinv) as an irreversible, chemoselective ligation reaction for that purpose. After having shown the efficiency of the DARinv in solution, we prepared a series of carbohydrate-dienophile conjugates that were printed onto tetrazine-modified glass slides. Binding experiments with fluorescently labeled lectins proved successful and homogeneous immobilization was achieved by the DARinv. For immobilization of nonfunctionalized reducing oligosaccharides we developed a bifunctional chemoselective linker that enabled the attachment of a dienophile tag to the oligosaccharides through oxime ligation. The conjugates obtained were successfully immobilized on glass slides. The presented strategies for the immobilization of both synthetic carbohydrate derivatives and unprotected reducing oligosaccharides facilitate the preparation of high-quality carbohydrate microarrays by means of the chemoselective DARinv. This concept can be readily adapted for the preparation of other biomolecule arrays. Copyright
- Beckmann, Henning S. G.,Niederwieser, Andrea,Wiessler, Manfred,Wittmann, Valentin
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supporting information; scheme or table
p. 6548 - 6554
(2012/06/30)
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- METHOD FOR HYDROFORMYLATION
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The present invention relates to a process for the hydroformylation of compounds of the formula (I), where X is C, P(Rx), P(O—Rx) S or S(═O), where Rx is H, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; A is a divalent bridging group having from 1 to 4 bridging atoms; and R1 is H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; or salts thereof; in which the compound of the formula (I) is reacted with carbon monoxide and hydrogen in the presence of a catalyst comprising a complex of a metal of transition group VIII with a compound of the formula (II), where Pn is a pnicogen atom; W is a divalent bridging group having from 1 to 8 bridging atoms; R2 is a functional group capable of forming an intermolecular, noncovalent bond with the group —X(═O)OH; R3, R4 are each alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; a, b, c are each 0 or 1; and Y1, Y2 and Y3 are each O, S, NRa or SiRbRc; and also compounds of the formula (II.a), where W′ is a divalent bridging group having from 1 to 5 bridging atoms between the flanking bonds, Z is O, S, S(═O), S(═O)2, N(RIX) or C(RIX)(RX); and RI to RX are each, independently of one another, H, halogen, nitro, cyano, amino, alkyl, etc.; or two radicals RI, RII, RIV, RVI, RVIII and RIX together represent the second part of a double bond.
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Page/Page column 9
(2010/10/03)
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- Copper-catalyzed olefin aminoacetoxylation
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A new catalyst system for intramolecular olefin aminoacetoxylation is described. In contrast to previously reported palladium- and copper-catalyzed systems, the conditions outlined in this communication favor piperdine formation with terminal olefin subst
- Mancheno, Danny E.,Thornton, Aaron R.,Stoll, Armin H.,Kong, Aidi,Blakey, Simon B.
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supporting information; experimental part
p. 4110 - 4113
(2010/11/04)
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- A supramolecular catalyst for regioselective hydroformylation of unsaturated carboxylic acids
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(Chemical Equation Presented) The quest to capture the catalytic power of enzymes is one of the great challenges of modern chemistry. A novel system inspired by the principles of enzymatic catalysis combines recognition of the substrate and transition-metal catalysis (see scheme; Do = donor, FG = functional group) and mimics enzyme properties - high efficiency, substrate selectivity, and reaction-site selectivity.
- Smejkal, Tomas,Breit, Bernhard
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p. 311 - 315
(2008/09/19)
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- Silicon-containing polyphilic bent-core molecules: The importance of nanosegregation for the development of chirality and polar order in liquid crystalline phases formed by Achiral molecules
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Polyphilic molecules composed of a bent aromatic core, oligo(siloxane) units, and alkyl segments were synthesized, and the self-organization of these molecules was investigated. Most materials organize into polar smectic liquid crystalline phases. The swi
- Keith, Christina,Reddy, R. Amaranatha,Hauser, Anton,Baumeister, Ute,Tschierske, Carsten
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p. 3051 - 3066
(2007/10/03)
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- Isomerization of cyclic ethers having a carbonyl functional group: New entries into different heterocyclic compounds
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Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group.
- Kanoh, Shigeyoshi,Naka, Masashi,Nishimura, Tomonari,Motoi, Masatoshi
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p. 7049 - 7064
(2007/10/03)
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- Synthesis of polyhydroxylated pyrrolizidine alkaloids of the alexine family by tandem ring-closing metathesis-transannular cyclization. (+)-Australine
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Dienes 23 and 54, prepared from epoxy alcohol 9 via oxazolidinones 15 and 51, respectively, underwent ring-closing metathesis with Grubbs's catalyst to give azacyclooctenes 26 and 55. Treatment of each azacyclooctene with m-chloroperoxybenzoic acid afforded β-epoxide 28 from 26 and α-epoxide 61 from 60. Basic hydrolysis of each of these oxazolidinones was accompanied by transannular attack at the epoxide by nitrogen, resulting in 2-(O-benzyl)-7-deoxyalexine (29) and 1,2-di-(O-benzyl)australine (62). The latter was converted to the alkaloid australine (3) upon hydrogenolysis. Attempts to effect ring-closing metathesis of dienes 37, 38, and 46 were unsuccessful, suggesting that, while one allylic oxygen substituent can be tolerated by Grubbs's catalyst, two cannot.
- White,Hrnciar
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p. 9129 - 9142
(2007/10/03)
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- A study of vinyl radical cyclization onto the azido group by addition of sulfanyl, stannyl, and silyl radicals to alkynyl azides
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Thermal radical reactions of azidoalkynes 2, 8, 14, and 21a-c with thiols 1a-c afford 2-sulfanylvinyl radicals by selective addition of sulfanyl radicals to the triple bond. 1-Phenylvinyl radicals 23 and 30a, as well as vinyl radical 30b, undergo fast 5-cyclization onto the aromatic azide function to give cyclized indoles. In contrast, both 1-phenyl (15, 17) and 1-alkyl (3a,b, 9) vinyl radicals fail to add to their aliphatic azido substituents and exclusively undergo cyclization onto the aromatic sulfanyl ring and H transfer from the thiol precursor. Azidoalkynes 14 and 21a react with Bu3SnH and TMSS under radical conditions to give instead the corresponding amines as a result of preferential attack of Bu3Sn · and (TMS)3Si · radicals on the azido group rather than on the triple bond. Evidence is provided that alkyl radical cyclizations onto azides are not feasible in the presence of thiol, in contrast with the reported utility of these cyclization reactions in the presence of Bu3SnH and TMSS.
- Montevecchi, Pier Carlo,Navacchia, Maria Luisa,Spagnolo, Piero
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p. 1219 - 1226
(2007/10/03)
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- 37. Synthesis of highly fluorinated di-O-alk(en)yl-glycerophospholipids and evaluation of their biological tolerance
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The syntheses of various fluorocarbon/fiuorocarbon and fluorocarbon/hydrocarbon rac-1,2- and 1,3-di-O-alk(en)ylglycerophosphocholines and rac-1,2-di-O-alkylglycerophosphoethanolamines (see Fig.2), which may be used as components for drug-carrier and delivery systems, are described together with some results concerning their biological tolerance. They were obtained by phosphorylation of perfluoroalkylated rac-di-O-alk(en)ylglycerols using POCl3, then condensation with choline tosylate or N-Boc-ethanolamine (2-[(tert-butoxy)carbonyl-amino]ethanol) followed by Boc-deprotection (Schemes 6-8). The fluorocarbon/fluorocarbon 1,2-di-O-alkylglycerols were prepared by O-alkylation of rac-1-O-benzylglycerol using perfluoroalkylated mesylates, then hydrogenolysis for benzyl deprotection (Scheme I). The two different hydrophobic chains in the mixed fluorocarbon/ fluorocarbon and fluorocarbon/hydrocarbon 1,2-di-O-alk(en)ylglycerols were introduced starting from 1,2-O-isopropylidene- then O-trityl-protected glycerols or from 1,3-O-benzylidene-glycerol (Schemes 3 and 4). The perfluoroalkylated O-alkenylglycerols were obtained by O-alkylation of a glycerol derivative using an ω-unsaturated alkenyl reagent, the perfluoroalkyl segment being connected onto the double bond in a subsequent step (Schemes 1 and 3) The perfluoroalkylated symmetrical and mixed 1,3-di-O-alkylglycerols were synthesized by displacement of the Cl-atom in epichlorohydrin by perfluoroalkylated alcohols, then catalytic (SnCl4) opening of the oxirane ring of the resulting alkyl glycidyl ethers in neat alcohols (Scheme 5). When injected intravenously into mice, acute maximum tolerated doses higher than 1500 and 2000 mg/kg body weight were observed for the fluorinated glycerophosphocholines, indicating a very promising in vivo tolerance.
- Ravily, Veronique,Gaentzler, Sylvie,Santaella, Catherine,Vierling, Pierre
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p. 405 - 425
(2007/10/03)
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- Ring closure reactions of substituted 4-pentenyl-1-oxy radicals. The stereoselective synthesis of functionalized disubstituted tetrahydrofurans
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N-(Alkyloxy)pyridine-2(1H)-thiones 3 and benzenesulfenic acid O-esters 5 have been synthesized from substituted 4-pentenols 1 or the derived tosylates. Compounds 3 and 5 are efficient sources of free alkoxy radicals 6 which undergo synthetically useful fast ring closure reactions 6 → 8 [k(exo) = (2 ± 1) x 108 s-1 to (6 ± 2) x 109 s-1 (T = 30 ± 0.2°C)]. Tetrahydrofurfuryl radicals 8 can be trapped with, e.g., hydrogen or chlorine atom donors to afford either trans- or cis-disubstituted tetrahydrofurans 10 or 12 depending on the substitution pattern of the 4-pentenyloxy radical. Substituted tetrahydropyrans 11 or 13 are formed in the minor 6-endo-trig cyclization. According to the data of competition kinetics, the observed stereoselectivities in free alkoxy radical cyclizations arise from steric interactions between the substituents in the transition state of the ring closure reactions. Alkyl substituents cause small differences in the measured relative rate constants of 5-exo cyclizations which are reminiscent of the data obtained from the rearrangements of alkyl-substituted 5-hexenyl radicals. Likewise, a stereochemical model for oxygen radical cyclization is proposed where the pentenyloxy chain adopts a six-membered, chairlike transition state with the alkyl substituents preferentially situated in the pseudoequatorial positions leading to 2,5-trans-, 2,4-cis-, and 2,3-trans-substituted tetrahydrofurfuryl radicals 8 as the major intermediates.
- Hartung,Gallou
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p. 6706 - 6716
(2007/10/03)
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- Characteristic odoriferous compounds of brown algae: Syntheses of possible oxidation products of (6Z,9Z,12Z,15Z)-1,6,9,12,15-heneicosapentaene and (6Z,9Z,12Z,15Z,18Z)-1,6,9,12,15,18-heneicosahexaene
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The unsaturated aldehydes (3Z,6Z)-3,6,11-dodecatrienal (9), (2E,4Z,7Z)-2,4,7,12-tridecatetraenal (10) and (3Z,6Z,9Z)-3,6,9,14-pentadecatetraenal (11) are expected to be products of the air oxidation of heneicosapentaene 1 and heneicosahexaene 2.The first attempts to synthesize aldehydes 9 and 11 (which failed) were based upon repeated Horner-Wittig reactions with phosphine oxide 12.In a second attempt, acetylene chemistry was applied to prepare aldehydes 9, 10 and 11.Their olfactive properties are described.
- Broekhof, Nico L.J.M.,Witteveen, Jan G.,Weerdt, Anton J. A. van der
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p. 436 - 442
(2007/10/02)
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