- Diels-Alder adducts of of ortho-benzoquinones: Rearrangements and further transformations
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ortho-Benzoquinones substituted with an electron-withdrawing group (EWG = CO2Me, COSMe, COCH3, CHO) at C-3 or C-4 react as dienophiles at the C3 - C4 double bond in Diels-Alder reactions with several dienes, with predictable regiochemistry. The adducts undergo migration of the "angular" EWG substituent with concomitant aromatization to produce substituted catechols. The bicyclic products can be oxidized in situ and annelated by a further Diels-Alder reaction to yield 9,10-phenanthraquinone systems. When (2E)-2,4-pentadienol is employed as the diene in the second cycloaddition, reaction of the alcoholic hydroxyl group with one of the quinone carbonyl groups results in the production of tetracyclic lactols 22a, 22b, and 23.
- Carlini, Rina,Higgs, Kerianne,Taylor, Nicholas,Rodrigo, Russell
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Read Online
- Method for preparing 1,3-pentadiene from xylitol
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The invention relates to a method for preparing 1,3-pentadiene from xylitol. The method is used for preparing 1,3-pentadiene from xylitol as a raw material and is divided into two steps of reactions:firstly, 2,4-pentadiene-1-ol formate is prepared from xylitol and formic acid through a deoxygenation and dehydration reaction and an esterification reaction without a catalyst; secondly, 1,3-pentadiene is prepared from 2,4-pentadiene-1-ol formate through a deoxygenation reaction under catalysis of a hydrogenation catalyst. The catalyst and the raw material are cheap and easily available, the preparation process is simple, an externally added hydrogen source is not needed, and higher activity and selectivity are realized in the deoxygenation and dehydration reaction of xylitol and deoxygenation reaction of 2,4-pentadiene-1-ol formate. The cheap and efficient method for synthesizing 1,3-pentadiene from xylitol as a lignocellulose-based platform chemical compound is provided.
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Paragraph 0028-0053
(2018/07/06)
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- Palladium-Promoted Neutral 1,4-Brook Rearrangement/Intramolecular Allylic Cyclization Cascade Reaction: A Strategy for the Construction of Vinyl Cyclobutanols
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A cascade reaction to build vinyl cyclobutanol rings through activation of vinyl epoxides by palladium, followed by 1,4-Brook rearrangement and intramolecular cyclization with a palladium complex of the resulting carbon anion, is described. Through this cascade reaction, several highly substituted cyclobutanol substrates were achieved in good yields with high stereoselectivities.
- Zhang, Hao,Ma, Shiqiang,Yuan, Ziyun,Chen, Peng,Xie, Xingang,Wang, Xiaolei,She, Xuegong
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supporting information
p. 3478 - 3481
(2017/07/15)
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- Production of renewable 1,3-pentadiene from xylitol via formic acid-mediated deoxydehydration and palladium-catalyzed deoxygenation reactions
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A two-step synthetic approach for the production of renewable 1,3-pentadiene was reported: xylitol deoxydehydration (DODH) by formic acid to 2,4-pentadien-1-ol, 1-formate (2E), followed by deoxygenation to 1,3-pentadiene over Pd/C. The overall carbon yield of 1,3-pentadiene reached 51.8% under the optimized conditions.
- Sun, Ruiyan,Zheng, Mingyuan,Li, Xinsheng,Pang, Jifeng,Wang, Aiqin,Wang, Xiaodong,Zhang, Tao
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supporting information
p. 638 - 642
(2017/02/26)
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- Intramolecular Parallel [4+3] Cycloadditions of Cyclopropane 1,1-Diesters with [3]Dendralenes: Efficient Construction of [5.3.0]Decane and Corresponding Polycyclic Skeletons
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Aiming to develop efficient and general strategies for construction of complex and diverse polycyclic skeletons, we have successfully developed [4+3]IMPC (intramolecular parallel cycloaddition) of cyclopropane 1,1-diesters with [3]dendralenes. With a combination of the [4+3]IMPC and subsequent [4+n] cycloadditions, trans-[5.3.0]decane skeleton and its corresponding structurally complex and diverse polycyclic variants could be constructed efficiently. This novel [4+3] cycloaddition reaction mode of donor–acceptor cyclopropanes proceeds as a result of the ring-strain relief of a trans-[3.3.0]octane. We strongly believe that the developed methods will demonstrate potential applications in natural products synthesis and drug discovery.
- Zhang, Chi,Tian, Jun,Ren, Jun,Wang, Zhongwen
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supporting information
p. 1231 - 1236
(2017/02/05)
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- Regioselective Epoxidations by Cytochrome P450 3A4 Using a Theobromine Chemical Auxiliary to Predictably Produce N-Protected β- or γ-Amino Epoxides
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N-Protected β- and γ-amino epoxides are useful chiral synthons. We report here that the enzyme cytochrome P450 3A4 can catalyze the formation of such compounds in a regio- and stereoselective manner, even in the presence of multiple double bonds or aromatic substituents. To this end, the theobromine chemical auxiliary is used not only to control the selectivity of the enzyme, but also as a masked amine, and to facilitate product recovery. Theobromine predictably directed epoxidation at the double bond of the fourth carbon from the theobromine group. Unlike with most catalysts, the selectivity did not depend on electronic or steric factors but rather on the position of the olefin relative to the theobromine group. (Figure presented.).
- Polic, Vanja,Cheong, Kin Jack,Hammerer, Fabien,Auclair, Karine
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supporting information
p. 3983 - 3989
(2017/11/30)
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- Oxo-rhenium-catalyzed deoxydehydration of polyols with hydroaromatic reductants
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Several dihydroaromatic compounds are shown to be effective reducing agents in the oxo-metal-catalyzed deoxydehydration of diols and polyols to produce olefins and the corresponding arenes. NH4ReO4 and MeReO3 are active catalysts for the reactions. The most effective of the hydroaromatic reductants is indoline, which is oxidized to indole. Yields for a variety of diols and polyols range from 35% to 99%. Two hydrogen donors, 1,3-cyclohexadiene and dihydroanthracene, engage in tandem DODH/cycloaddition reactions. Competition experiments show that indoline is more reactive than representative alcohols in H-transfer. Indoline is shown to reduce MeReO3 to MeReO2 via an isolable adduct, MeReO3(indoline) (4), which has been structurally characterized and is suggested to be an intermediate in the catalytic DODH process.
- Boucher-Jacobs, Camille,Nicholas, Kenneth M.
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supporting information
p. 1985 - 1990
(2015/06/08)
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- Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization
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The synthesis of spiroindanes by the palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes with 2-aryl cyclic 1,3-dicarbonyl compounds is described. Examples of the dearomatizing oxidative annulation of 1,3-dienes with 1-aryl-2-naphthols are also presented. This journal is
- Khan, Imtiaz,Chidipudi, Suresh Reddy,Lam, Hon Wai
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supporting information
p. 2613 - 2616
(2015/03/05)
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- Through-bond/through-space anion relay chemistry exploiting vinylepoxides as bifunctional linchpins
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The development of new bifunctional linchpins that permit the union of diverse building blocks is essential for the synthetic utility of anion relay chemistry (ARC). The design, synthesis, and validation of three vinylepoxide linchpins for through-bond/through-space ARC are now reported. For negative charge migration, this class of bifunctional linchpins employs initial through-bond ARC by an SN2' reaction, followed by through-space ARC exploiting a 1,4-Brook rearrangement. The trans-disubstituted vinylepoxide linchpin yields a mixture of E/Z isomers, whereas the cis-disubstituted and the trans-trisubstituted vinylepoxide linchpins proceed to deliver three-component adducts with excellent E selectivity.
- Chen, Ming Z.,Gutierrez, Osvaldo,Smith, Amos B.
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supporting information
p. 1279 - 1282
(2014/03/21)
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- Simple and efficient 1,3-isomerization of allylic alcohols using a supported monomeric vanadium-oxide catalyst
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Promotion by group high five: Silica-supported monomeric vanadium-oxide promoted the isomerization of various allylic alcohols, including under scaled-up and solvent-free reaction conditions. This catalyst also exhibited high reusability with no drop in activity.
- Mitsudome, Takato,Sueoka, Shoichiro,Ikeda, Satoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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p. 2879 - 2882
(2013/10/21)
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- Diastereocontrol in asymmetric allyl-allyl cross-coupling: Stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides
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Palladium-catalyzed allyl-allyl cross-coupling was investigated with substituted prochiral allylic boronates. These reactions deliver products bearing adjacent stereocenters, and the issue of diastereocontrol is therefore paramount. Under appropriately mo
- Brozek, Laura A.,Ardolino, Michael J.,Morken, James P.
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supporting information; scheme or table
p. 16778 - 16781
(2011/12/04)
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- Organic Compounds
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The invention refers to conjugated secondary alkatrienol derivatives, a method of their production and to flavour and perfume compositions comprising them.
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Page/Page column 2
(2010/08/07)
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- Efficient silver-catalyzed regio- and stereospecific aziridination of dienes
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Nitrene transfer: Unsymmetric dienes bearing a terminal hydroxy group can be regio- and stereospecifically converted into vinylaziridines upon nitrene transfer from PhINTs using a silver-based catalyst. Stoichiometric mixtures of dienes and PhINTs were employed at low catalyst loadings (0.5□%; see scheme). The method has been applied to the synthesis of (±)-sphingosine and gave good yields in a three-step procedure. Ts=4-toluenesulfonyl.
- Llaveria, Josep,Beltran, Alvaro,Diaz-Requejo, M. Mar,Perez, Pedro J.,Matheu, M. Isabel,Castillon, Sergio
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supporting information; experimental part
p. 7092 - 7095
(2010/11/05)
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- Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration
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(Chemical Equation Presented) Asymmetric 1,4-dihydroxylations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B2(pin) 2) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyclic substrates will participate in this reaction; however, dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway. In addition to oxidation to the derived 2-buten-1,4-diol, stereoselective carbonyl allylation with the intermediate bis(boronate) ester is also described.
- Burks, Heather E.,Kliman, Laura T.,Morken, James P.
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supporting information; scheme or table
p. 9134 - 9135
(2009/12/05)
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- (+)-Rimocidin synthetic studies: Construction of the C(1-27) aglycone skeleton
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(Chemical Equation Presented) Assembly of the C(1-27) macrocyclic skeleton of rimocidinolide, the aglycone of (+)-rimocidin (1), has been achieved in convergent fashion. Key features of the synthetic strategy entail application of multicomponent Type I Anion Relay Chemistry (ARC), in conjunction with the SN2/SN2′ reaction manifolds of vinyl epoxides, both employing 2-substituted 1,3-dithianes to construct the C(1-19) carbon backbone. Yamaguchi union of a C(20-27) vinyl borate ester, possessing the all-trans triene, with an advanced C(1-19) vinyl iodide followed by macrocyclization via Suzuki-Miyaura crosscoupling completed construction of the C(1-27) rimocidinolide skeleton.
- Smith III, Amos B.,Foley, Megan A.,Dong, Shuzhi,Orbin, Alia
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experimental part
p. 5987 - 6001
(2009/12/26)
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- Cu(I)-catalyzed stereospecific coupling reactions of enantioenriched α-stannylated benzyl carbamates and their application
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Enantioenriched α-stannylated benzyl carbamates were used in highly stereospecific coupling reactions employing Cu(I) as catalyzing transition metal. Acid chlorides and allyl bromide derivatives were used as electrophilic coupling partners. The reaction w
- Lange, Heiko,Fr?hlich, Roland,Hoppe, Dieter
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p. 9123 - 9135
(2008/12/22)
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- Total synthesis of siphonazole and its O-methyl derivative, structurally unusual bis-oxazole natural products
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The details of the first syntheses of the unusual bis-oxazole natural products siphonazole and its O-methyl derivative are reported. The cinnamyl substituted oxazole was constructed using diazocarbonyl chemistry, whereby the cinnamamide was reacted with the rhodium carbene derived from methyl 2-diazo-3-oxobutanoate to give a β-ketoamide that was cyclodehydrated to the corresponding oxazole-4-ester. Reduction to the corresponding aldehyde was followed by coupling with a zinc reagent derived from methyl 2-iodomethyl-5-methyloxazole-4-carboxylate, also prepared using rhodium carbene chemistry, to give, after oxidation of the resulting secondary alcohol, the desired bis-oxazole ketone. The syntheses were completed by hydrolysis of the ester and coupling of the 2,4-pentadienylamine side chain. The 2008 Royal Society of Chemistry.
- Linder, Joerg,Blake, Alexander J.,Moody, Christopher J.
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supporting information; experimental part
p. 3908 - 3916
(2009/06/28)
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- Silenes in organic synthesis: A concise synthesis of (±)-epi- picropodophyllin
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A concise, seven step synthesis of the aryl tetralin lignan lactone epi-picropodophyllin from piperonal is described. The key steps are a silene diene Diels-Alder reaction and the Hosomi-Sakurai reaction of the resultant silacyclohexene. The Royal Society
- Pullin, Robert D. C.,Sellars, Jonathan D.,Steel, Patrick G.
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p. 3201 - 3206
(2008/04/01)
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- The total synthesis of the oxopolyene macrolide RK-397
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It works both ways: The convergent total synthesis of the oxopolyene macrolide RK-397 utilizes remote asymmetric induction and a two-directional chain synthesis to prepare the polyol portion of the molecule, as well as a cross-metathesis reaction of a trienal with a terminal alkene to append the polyene to the polyol. (Chemical Equation Presented).
- Mitton-Fry, Mark J.,Cullen, Aaron J.,Sammakia, Tarek
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p. 1066 - 1070
(2008/03/14)
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- Core structure of eremophilanes and bakkanes through niobium catalyzed Diels-Alder reaction: Synthesis of (±)-bakkenolide A
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A suitable intermediate for the synthesis of eremophilanes and bakkanes was prepared by a highly regioselective and stereoselective one-step synthesis through a niobium catalyzed Diels-Alder reaction. As a demonstration of the versatility of this intermed
- Constantino, Mauricio G.,De Oliveira, Kleber T.,Polo, Ellen C.,Da Silva, Gil V. J.,Brocksom, Timothy J.
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p. 9880 - 9883
(2007/10/03)
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- Liquid-phase isomerization of saturated and unsaturated epoxides
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The liquid-phase isomerization of a variety of epoxides was studied using a complex catalyst system based on magnesium bromide and dimethylformamide. The data obtained elucidate the mechanism of the liquid-phase isomerization and show the range of oxygen-containing compounds which can be prepared through this reaction.
- Mel'nik,Khvatova,Moskvichev,Srednev,Egorova
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p. 167 - 169
(2007/10/03)
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- Synthesis of oxygen-containing compounds from 1,4-pentadiene
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1,4-Pentadiene oxidation with pinane and cumene hydroperoxides was examined. The application of crude cumene hydroperoxide was shown to yield 90% 1,2-epoxypentene-4 at an oxidant conversion of over 95%. The isomerization of 1,2-epoxypentene-4 in the vapor phase at 290-330°C on lithium phosphate was studied. The rearrangement yielded 2,4-pentadiene-1-ol and unsaturated carbonyl compounds in a nearly 1:1 ratio at an epoxide conversion of 50%. Carbonyl compounds consisted mainly of pentenals with a different double-bond position. The results of the rearrangement show that the epoxide C-O bond heterolysis takes place mainly on the allyl group side.
- Srednev,Yas'Kina,Moskvichev,Egorova,Shutova,Kozlova
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- Pentadienyl type lithium and potassium species: The regioselectivity of their reactions with electrophiles
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Seven structurally distinct pentadienyl type lithium and potassium compounds were screened against a variety of electrophiles in order to assess the regioselectivity of the trapping reactions. Organoborates and analogs thereof (fluorodimethoxyborane) proved to be perfectly regioreliable attacking only unsubstituted terminal positions and thus providing, after oxidation, exclusively primary allylic alcohols. 2,4-Pentadienyllithiums or -potassiums, that carry a methyl group at the 1- or 3-position, exhibit the same extreme regioselectivity towards halotrialkylsilanes or carbon dioxide. Although the unsubstituted parent compounds combine with such electrophiles still preferentially at the terminal position, considerable proportions of branched products are concomitantly formed as well (1/3-attack ratios ranging from 2:1 to >20:1). Hydroxyalkylating and alkylating reagents such as formaldehyde, oxirane or butyl iodide invariably afford regioisomeric mixtures generally varying in composition between 3:1 and 1:3. The condensation reaction with halotrialkylsilanes appears to follow a concerted (SN2-like) rather than an addition/elimination (ate complex-mediated) mechanism.
- Schlosser,Zellner,Leroux
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p. 1830 - 1836
(2007/10/03)
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- Development of a method for the synthesis of α-substituted α,β- unsaturated lactones based on stille-type Pd-catalyzed carbonylation of (Z)- ω-iodoalkenols. An efficient and selective synthesis of (+)-hamabiwalactone B
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Pd-Catalyzed carbonylative lactonization of (Z)-ω-iodoalkenols can be applied to synthesize α/β-unsaturated lactones containing an alkenyl or alkynyl substituent in the α position, providing a generally superior alternative to recently developed methods involving Pd-catalyzed α- substitution of α-stannyl esters, as exemplified by a highly expeditious synthesis of (+)-hamabiwalactone B.
- Liao, Baiqiao,Negishi, Ei-Ichi
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p. 1241 - 1249
(2007/10/03)
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- Synthetic studies on clerodane diterpenoids. 3. An alternative synthesis of an unnatural antifeedant
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An alternative synthesis of (1S*,2S*,6R*,10S*)-2-acetoxy-1-acetoxymethyl-5,5- dimethylbicyclo[4.4.0]decane-10-spiro-2′-oxirane (1), an unnatural antifeedant, has been effected via an intermolecular Diels-Alder approach.
- Liu, Hsing-Jang,Al-Said, Naim H.
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p. 203 - 207
(2007/10/03)
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- Intramolecular Diels-Alder Reactions of Silyl Acetal-tethered Trienes
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The synthesis and intramolecular Diels-Alder reactions of a series of silyl acetal-tethered trienes 4-9 are described.The cycloadditions show complete regioselectivity, and in all but one case give exclusively cis-fused bicyclic products.The selectivities
- Ainsworth, Peter J.,Craig, Donald,Reader, John C.,Slawin, Alexandra M. Z.,White, Andrew J. P.,Williams, Dawid J.
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p. 11601 - 11622
(2007/10/02)
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- COMPOUNDS WITH HERBAL ODOR. V. UNBRANCHED PRIMARY (Z)-ALKENOLS
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The similarity between the odor of alkenols (Z)-CH3-(CH2)n(H=CH(CH2)mOH and the odor of leaf alcohol (m=2, n=1), taken as standard, gradually weakened with change in the m and/or n values and is determined by the number of carbon atoms in the molecules.
- Vasil'ev, A. A.,Cherkaev, G. V.,Nikitina, M. A.
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p. 735 - 739
(2007/10/02)
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- STEREOCHEMICAL ASPECTS OF THE HYDROALUMINATION-IODINATION OF α-ENYNYL ALCOHOLS AND SUBSTITUTIVE METHYLATION OF 3-IODO-2,4-ALKADIEN-1-OLS WITH DIMETHYLCOPPERLITHIUM
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The hydroalumination-iodination of α-enynyl alcohols leads to a mixture of E- and Z-iododienols.Almost total inversion (ca. 90percent) of the configuration was unexpectedly discovered during the nucleophilic methylation of Z-3-iodo-2,4-alkadien-1-ols.The synthesis of Z-tagetol (the synthetic precursor of Z-tagetone) was realized.According to the 1H and 13C NMR and UV spectra and conformational analysis, the double bonds of the 1,3-diene group in the obtained compounds are not coplanar.The stereochemical features of both stages were interpreted in relation to the steric characteristics of the configurationally unstable organometallic diene derivatives.
- Khrimyan, A. P.,Garibyan, O. A.,Panosyan, G. A.,Mailyan, N. Sh.,Kinoyan, F. S.,et al.
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p. 1961 - 1973
(2007/10/02)
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- Novel Synthesis of Phenol Derivatives by Palladium-Catalyzed Cyclocarbonylation of 2,4-Pentadienyl Acetates
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Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140 deg C under 50 atm of CO.No five-membered ring products were observed.A platinum complex PtCl2(PPh3)2 was also effective as a catalyst.The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3,5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51percent yield on heating to 160 deg C under 50 atm of CO in the presence of NEt3 and Ac2O.Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates.On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO, respectively.
- Ishii, Youichi,Gao, Chao,Xu, Wen-Xiang,Iwasaki, Masakazu,Hidai, Masanobu
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p. 6818 - 6825
(2007/10/02)
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- and Thermal Sigmatropic Rearrangements of 2-Pentadienyloxypyridine N-Oxides
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2-Pentadienyloxypyridine N-oxides (3) are smoothly transformed on heating into N-pentadienyloxy-2-pyridones (4) and N-hydroxy-5-pentadienyl-2-pyridones (5).These reactions are shown to be regiospecific and are believed to proceed in a concerted fashion.Th
- Alker, David,Ollis, W. David,Shahriari-Zavareh, Hooshang
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p. 1637 - 1643
(2007/10/02)
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- STEREOSELECTIVE SN2' ADDITIONS OF ORGANOCUPRATES TO HOMOCHIRAL ACYLIC VINYLOXIRANES
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Additions of various methylcopper reagents to the homochiral acylic vinyloxiranes A14, A15, B6-B9, and C5, C6 were performed in order to evaluate E/Z and syn/anti preferences.The unsubstituted oxiranes A14 and A15 gave a mixture of SN2 and SN2' substitution products with the four reagents examined, LiMe2Cu, LiMeCuCN, BrMgMe2Cu, and LiMeCuI*BF3.The more highly substituted systems B6-B9 derived from geraniol and C5, C6 derived from nerol yielded only SN2' products.The (Z)-allylic alcohol derivatives B8 and C6 and LiMeCuCN gave the best anti/syn ratios (99:1 and 97:3, respectively).In both cases the newly formed double bond was exclusively E.
- Marshall, James A.,Trometer, Joseph D.,Cleary, Darryl G.
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p. 391 - 402
(2007/10/02)
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- The Use of Dichloromaleic and Bromomaleic Anhydrides in the Synthesis of Lactones by the Intramolecular Diels-Alder Reaction
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Reaction of (E)-penta-2,4-dien-1-ol with dichloromaleic anhydride gives an unstable triene, which on heating undergoes an intramolecular Diels-Alder cyclisation to give a bicyclic acid, which on dechlorodecarboxylation affords an unsaturated bicyclic lact
- Batchelor, Mark J.,Mellor, John M.
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p. 985 - 995
(2007/10/02)
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- ISOLATION, IDENTIFICATION AND SYNTHESIS OF SEX PHEROMONE COMPONENTS OF THE CAROB MOTH, ECTOMYELOIS CERATONIAE
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The sex pheromone of females of the carob moth, Ectomyelois ceratoniae, was identified to be a mixture of (Z,E)-9,11,13-tetradecatrienal, (Z,E)-9,11-tetradecadienal and (Z)-9-tetradecenal in the ratio of 10:1:1.A synthetic blend proved to be attractive.
- Baker, T. C.,Francke, W.,Loefstedt, C.,Hansson, B. S.,Du, J.-W.,et al.
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p. 2901 - 2902
(2007/10/02)
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- STEREOSELECTIVE SN2' ADDITIONS TO CHIRAL ACYCLIC VINYLOXIRANES
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Additions of LiMe2Cu to acyclic vinyloxiranes 4, 5, 6 and 7 proceed predominately anti SN2' to afford the (E)-allylic alcohol products.
- Marshall, James A.,Trometer, Joseph D.
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p. 4985 - 4988
(2007/10/02)
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- Conjugated dienols
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Conjugated dienols for providing cure sites to air-drying acrylic finishes are prepared from conjugated dienoic acids by conversion to an activated ester followed by sodium borohydride reduction thereof.
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