cas 5675-51-4, 1,12-Dodecanediol | Articles data

Articles about 5675-51-4Total 36 be found

Article title
Article abstract
Author
Journal number and time
Download

MELYNES, POLYACETYLENE CONSTITUENTS FROM A VANUATU MARINE SPONGE
The structures of three long chain polyeneyne triols, melynes A, B, C are established from degradation reactions, from NMR data and from extensive HREIMS data.
Quinoa, Emilio,Crews, Phillip
p. 2037 - 2040
(1988)
Read Online

A Macrocyclic Tetraether Bolaamphiphile and an Oligoamino α,ο-Dicarboxylate Combine To Form Monolayered, Porous Vesicle Membranes, Which Are Reversibly Sealed by EDTA and Other Bulky Anions
The hydrophobic tetraether macrocycle 1,20-disulfonyl-4,17,23,36-tetraoxacyclooctatriacontane is obtained in the gram scale from 2,2-dithioethanol and 1,12-dodecanediol.Oxidation or methylation of the sulfur atoms leads to bolaamphiphiles which vesiculate on ultrasonication.These amphiphiles are simple analogues of the membrane constituents of archaebacteria.The vesicles are acid stable and entrap metal ions (Li+, Fe2+) as well as fluorescent dyes (pyranine, calcein).The dipotassium salt of 2,19-dimethyl-3,6,9,12,15,18-hexaazaeicosanedicarboxylate introduces pores for metal ions into the membrane, but not for the organic dyes.The caionic pores could be closed with water-soluble bulky anions such as camphorsulfonic acid, taurine, and EDTA.The EDTA stopper was extracted from the pore by an excess of Fe(II) ions.Excess of EDTA reclosed the pore.This cycle could be repeated several times.
Fuhrhop, Juergen-Hinrich,Liman, Ulrich,Koesling, Volker
p. 6840 - 6845
(1988)
Read Online

Multi-enzymatic cascade reactions with Escherichia coli-based modules for synthesizing various bioplastic monomers from fatty acid methyl esters?
Multi-enzymatic cascade reaction systems were designed to generate biopolymer monomers using Escherichia coli-based cell modules, capable of carrying out one-pot reactions. Three cell-based modules, including a ω-hydroxylation module (Cell-Hm) to convert fatty acid methyl esters (FAMEs) to ω-hydroxy fatty acids (ω-HFAs), an amination module (Cell-Am) to convert terminal alcohol groups of the substrate to amine groups, and a reduction module (Cell-Rm) to convert the carboxyl groups of fatty acids to alcohol groups, were constructed. The product-oriented assembly of these cell modules involving multi-enzymatic cascade reactions generated ω-ADAs (up to 46 mM), α,ω-diols (up to 29 mM), ω-amino alcohols (up to 29 mM) and α,ω-diamines (up to 21 mM) from 100 mM corresponding FAME substrates with varying carbon chain length (C8, C10, and C12). Finally 12-ADA and 1,12-diol were purified with isolated yields of 66.5% and 52.5%, respectively. The multi-enzymatic cascade reactions reported herein present an elegant ‘greener’ alternative for the biosynthesis of various biopolymer monomers from renewable saturated fatty acids.
Jung, Hyunsang,Kim, Byung-Gee,Kim, Ye Chan,Park, Beom Gi,Patil, Mahesh D.,Sarak, Sharad,Yoo, Hee-Wang,Yun, Hyungdon
supporting information
p. 2222 - 2231
(2022/04/03)

Novel insights into oxidation of fatty acids and fatty alcohols by cytochrome P450 monooxygenase CYP4B1
CYP4B1 is an enigmatic mammalian cytochrome P450 monooxygenase acting at the interface between xenobiotic and endobiotic metabolism. A prominent CYP4B1 substrate is the furan pro-toxin 4-ipomeanol (IPO). Our recent investigation on metabolism of IPO related compounds that maintain the furan functionality of IPO while replacing its alcohol group with alkyl chains of varying structure and length revealed that, in addition to cytotoxic reactive metabolite formation (resulting from furan activation) non-cytotoxic ω-hydroxylation at the alkyl chain can also occur. We hypothesized that substrate reorientations may happen in the active site of CYP4B1. These findings prompted us to re-investigate oxidation of unsaturated fatty acids and fatty alcohols with C9–C16 carbon chain length by CYP4B1. Strikingly, we found that besides the previously reported ω- and ω-1-hydroxylations, CYP4B1 is also capable of α-, β-, γ-, and δ-fatty acid hydroxylation. In contrast, fatty alcohols of the same chain length are exclusively hydroxylated at ω, ω-1, and ω-2 positions. Docking results for the corresponding CYP4B1-substrate complexes revealed that fatty acids can adopt U-shaped bonding conformations, such that carbon atoms in both arms may approach the heme-iron. Quantum chemical estimates of activation energies of the hydrogen radical abstraction by the reactive compound 1 as well as electron densities of the substrate orbitals led to the conclusion that fatty acid and fatty alcohol oxidations by CYP4B1 are kinetically controlled reactions.
Thesseling, Florian A.,Hutter, Michael C.,Wiek, Constanze,Kowalski, John P.,Rettie, Allan E.,Girhard, Marco
(2019/12/12)

Preparation of a Series of Supported Nonsymmetrical PNP-Pincer Ligands and the Application in Ester Hydrogenation
In contrast to their symmetrical analogues, nonsymmetrical PNP-type ligand motifs have been less investigated despite the modular pincer structure. However, the introduction of mixed phosphorus donor moieties provides access to a larger variety of PNP ligands. Herein, a facile solid-phase synthesis approach towards a diverse PNP-pincer ligand library of 14 members is reported. Contrary to often challenging workup procedures in solution-phase, only simple workup steps are required. The corresponding supported ruthenium-PNP catalysts are screened in ester hydrogenation. Usually, industrially applied heterogeneous catalysts require harsh conditions in this reaction (250–350 °C at 100–200 bar) often leading to reduced selectivities. Heterogenized reusable Ru-PNP catalysts are capable of reducing esters and lactones selectively under mild conditions.
Konrath, Robert,Spannenberg, Anke,Kamer, Paul C. J.
supporting information
p. 15341 - 15350
(2019/11/14)

Hydrofunctionalization of Olefins to Higher Aliphatic Alcohols via Visible-Light Photocatalytic Coupling
Abstract: An atomically economical green protocol for the hydrofunctionalization of olefins to higher aliphatic alcohols with 100% anti-Markovnikov regioselectivity was developed via visible-light photocatalytic coupling. This method employs cheap, readily available and abundant methanol as both the C1 feedstock and the hydrogen source under visible light irradiation over CdS photocatalyst. A wide scope of olefin substrates could be hydrofunctionalized successfully to the corresponding higher alcohols with high selectivity. Besides alcohol, acetone and acetonitrile can also couple with olefins to generate the corresponding hydrofunctionalization products, suggesting promising potential industrial application. Graphical Abstract: [Figure not available: see fulltext.] Hydrofunctionalization of olefins to value-added chemicals with high selectivity was achieved via visible-light photocatalytic cross-coupling.
Bao, Jingxian,Fan, Yonghui,Zhang, Shuyi,Zhong, Liangshu,Wu, Minghong,Sun, Yuhan
(2019/04/14)

Renewable Polyethers via GaBr3-Catalyzed Reduction of Polyesters
Herein, a novel approach is reported for the synthesis of medium- and long-chain aliphatic polyethers 2 based on the GaBr3-catalysed reduction of polyesters 1 with TMDS as the reducing agent. Thus, various linear and branched aliphatic polyesters 1 were prepared and systematically investigated for this reduction strategy, demonstrating the applicability and versatility of this new polyether synthesis protocol. Medium- and long-chain chain polyethers were obtained from the respective polyesters without or with minor chain degradation, whereas short-chain polyesters, such as poly-l-lactide 1 i and poly[(R)-3-hydroxybutanoate] 1 j, showed major chain degradation. In this way, previously unavailable and uncommon polyethers were obtained and studied.
Dannecker, Patrick-Kurt,Biermann, Ursula,von Czapiewski, Marc,Metzger, Jürgen O.,Meier, Michael A. R.
supporting information
p. 8775 - 8779
(2018/07/14)

Pellynols M?O, cytotoxic polyacetylenic alcohols from a Niphates sp. marine sponge
Three new polyacetylenic alcohols, pellynols M?O (1–3), along with two known ones, melyne A (4) and melyne B (5), were isolated from a Niphates sp. marine sponge collected off the South China Sea. The structures of new compounds were determined based on a combination of 1D and 2D NMR analysis, ESI-MSn fragmentation, and chemical (ozonolysis) method. Their absolute configurations were assigned by modified Mosher's method. All the isolates showed potent cytotoxic activity against PC9 and HepG2 human cancer cell lines with IC50 values of 2.9–7.6 μM.
Wang, Jie,Liu, Li-Yun,Liu, Lei,Zhan, Kai-Xuan,Jiao, Wei-Hua,Lin, Hou-Wen
p. 3701 - 3706
(2018/05/25)

Tandem Reductive Hydroformylation of Castor Oil Derived Substrates and Catalyst Recycling by Selective Product Crystallization
An orthogonal tandem catalytic system consisting of rhodium and ruthenium complexes yielded linear C12 α,ω-bifunctional compounds from commercial, castor oil derived renewable substrates. With aldehyde yields up to 88 % and selectivities to the linear species of up to 95 %, this approach is direct and atom economic and provides easy access to potential polymer precursors for polycondensates. Additionally, a straightforward method for selective product crystallization was developed, which enabled recycling of the tandem catalytic system for two runs with excellent activity and simultaneously provided a high-purity product.
Furst, Marc R. L.,Korkmaz, Vedat,Gaide, Tom,Seidensticker, Thomas,Behr, Arno,Vorholt, Andreas J.
p. 4319 - 4323
(2017/12/15)

A new route to α,ω-diamines from hydrogenation of dicarboxylic acids and their derivatives in the presence of amines
A new and selective route for the synthesis of polymer precursors, primary diamines or N-substituted diamines, from dicarboxylic acids, diesters, diamides and diols using a Ru/triphos catalyst is reported. Excellent conversions and yields are obtained under optimised reaction conditions. The reactions worked very well using 1,4-dioxane as solvent, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. This method provides a potential route to converting waste biomass to value added materials. The reaction is proposed to go through both amide and aldehyde pathways.
Shi, Yiping,Kamer, Paul C. J.,Cole-Hamilton, David J.
supporting information
p. 5460 - 5466
(2017/11/22)

From intermolecular interactions to texture in polycrystalline surfaces of 1,ω-alkanediols (ω = 10–13)
Differences on herringbone molecular arrangement in two forms of long-chain 1,?-alkanediols (CnH2n+2O2 with n = 10, 11, 12, 13) are explained from the analysis of O-H···O hydrogen-bond sequences in infinite chains and the role of a C-H···O intramolecular hydrogen-bond in stabilization of a gauche defect, as well as the inter-grooving effectiveness on molecular packing. GIXD (Glancing Incidence X-ray Diffraction) experiments were conducted on polycrystalline monophasic samples. Diffracted intensities were treated with the multi-axial March-Dollase method to correlate energetic and geometrical features of molecular interactions with the crystalline morphology and textural pattern of samples. The monoclinic (P21/c, Z = 2) crystals of the even-numbered members (n = 10, 12; DEDOL and DODOL, respectively) are diametrical prisms with combined form {104}/{-104}/{001} and present a two-fold platelet-like preferred orientation, whereas orthorhombic (P212121, Z = 4) odd-numbered members (n = 11, 13; UNDOL and TRDOL, respectively) present a dominant needle-like orientation on direction [101] (fiber texture). We show that crystalline structures of medium complexity and their microstructures can be determined from rapid GIXD experiments from standard radiation, combined with molecular replacement procedure using crystal structures of compounds with higher chain lengths as reference data.
Luis-Raya, Gilgamesh,Ramírez-Cardona, Màrius,Luna-Bárcenas, Gabriel,Hernández-Landaverde, Martín A.,Jiménez-Nieto, Adair,García-Rivas, Jose Luis,Espa A-Sánchez, Beatriz Liliana,Sanchez, Isaac C.
(2017/06/28)

TRANSFORMATION OF PEROXYACETAL INTERMEDIATE
A method for transforming a compound of formula IIa: to a compound of formula III: is provided, wherein A is a C6-C10 alkene chain with at least one double bond, R1 is a C1-C10 alkyl, and R3 is an oxygen-containing functional group.
-
Paragraph 00260

(2015/06/03)

ACYCLIC ALKENES VIA OZONOLYSIS OF MULTI-UNSATURATED CYCLOALKENES
A method of making a compound of formula (IIa) by selective ozonolysis of a compound of formula (I) is provided, wherein A is a C6-C10 alkene chain with at least one double bond, R1 is a C1-C10 alkyl, and R3 is an oxygen-containing functional group.
-
(2015/02/02)

SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.
-
Paragraph 0299; 0300

(2016/01/30)

Tandem decarboxylative hydroformylation-hydrogenation reaction of α,β-unsaturated carboxylic acids toward aliphatic alcohols under mild conditions employing a supramolecular catalyst system
A new atom economic catalytic method for a highly chemoselective reduction of α,β-unsaturated carboxylic acids to the corresponding saturated alcohols under mild reaction conditions, compatible with a wide range reactive functional groups, is reported. The new methodology consists of a novel tandem decarboxylative hydroformylation/aldehyde reduction sequence employing a unique supramolecular catalyst system.
Diab, Lisa,Gellrich, Urs,Breit, Bernhard
supporting information
p. 9737 - 9739
(2013/10/21)

PROCESS FOR PRODUCING DODECANE-1, 12-DIOL BY REDUCTION OF LAURYL LACTONE PRODUCED FROM THE OXIDATION OF CYCLODODECANONE
A process for synthesizing dodecane-1,12-diol, and by-products thereof, by the reduction of lauryl lactone produced from the oxidation of cyclododecanone.
-
Paragraph 00131

(2013/08/15)

Selective switchable iron-catalyzed hydrosilylation of carboxylic acids
Selective reduction of carboxylic acids either to aldehydes or alcohols is achieved using a one pot procedure based on iron-catalyzed hydrosilylations. Using phenylsilane and (COD)Fe(CO)3 catalyst under UV-irradiation at rt, alcohols were obtained specifically in good yields, whereas aldehydes were selectively obtained using TMDS and (t-PBO)Fe(CO)3 catalyst under thermal activation.
Misal Castro, Luis C.,Li, Haoquan,Sortais, Jean-Baptiste,Darcel, Christophe
supporting information
p. 10514 - 10516,3
(2020/09/02)

METHOD FOR PRODUCING ALCOHOL COMPOUND
Provided is a method for producing an alcohol compound, which enables the alcohol compound to be obtained at a high yield from an amide compound or amine compound. The method for producing an alcohol compound, which is characterized by comprising allowing an alcohol in a supercritical state to act on the amide compound or amine compound in the presence of a carboxylic acid derivative to obtain the alcohol compound.
-
Page/Page column 11

(2012/06/18)

Regioselective ω-hydroxylation of medium-chain n-alkanes and primary alcohols by CYP153 enzymes from Mycobacterium marinum and Polaromonas sp. strain JS666
The oxofunctionalization of saturated hydrocarbons is an important goal in basic and applied chemistry. Biocatalysts like cytochrome P450 enzymes can introduce oxygen into a wide variety of molecules in a very selective manner, which can be used for the synthesis of fine and bulk chemicals. Cytochrome P450 enzymes from the CYP153A subfamily have been described as alkane hydroxylases with high terminal regioselectivity. Here we report the product yields resulting from C5-C12 alkane and alcohol oxidation catalyzed by CYP153A enzymes from Mycobacterium marinum (CYP153A16) and Polaromonas sp. (CYP153A P. sp.). For all reactions, byproduct formation is described in detail. Following cloning and expression in Escherichia coli, the activity of the purified monooxygenases was reconstituted with putidaredoxin (CamA) and putidaredoxin reductase (CamB). Although both enzyme systems yielded primary alcohols and α,ω-alkanediols, each one displayed a different oxidation pattern towards alkanes. For CYP153A P. sp. a predominant ω-hydroxylation activity was observed, while CYP153A16 possessed the ability to catalyze both ω-hydroxylation and α,ω- dihydroxylation reactions.
Scheps, Daniel,Honda Malca, Sumire,Hoffmann, Helen,Nestl, Bettina M.,Hauer, Bernhard
scheme or table
p. 6727 - 6733
(2011/11/30)

The preparation of three new partially deuterated hexadecanethiols for applications in surface chemistry
The synthesis of three partially deuterated hexadecanethiols has been achieved. Thiols CH3(CH2)7(CD2) 8SH, CD3(CD2)7(CH2) 8SH and CD3(CH2)15SH were targeted, as these compounds, after formation of self-assembled monolayers on Au(1 1 1) or Au nanoparticles, can provide mechanistic information pertaining to reactive atom migrations within the assembly. The syntheses of each of these compounds called upon Grignard coupling chemistry, which was activated by Li 2CuCl4. Applicable deuterium containing fragments were either commercially obtained or constructed from by way of an inexpensive and efficient ring opening, protection and dimerization of THF-d8. Sulfur incorporation was by thiolacetate substitution or addition reactions. The protocols presented possess general applicability in a number of syntheses requiring block-deuterated fattyalkyl sections. Copyright
Sheepwash, Erin E.,Rowntree, Paul A.,Schwan, Adrian L.
experimental part
p. 391 - 398
(2009/04/07)

General synthesis and aggregation behaviour of a series of single-chain 1,ω-Bis(phosphocholines)
The synthesis and physicochemical characterisation of a series of polymethylene-1,ω-bis(phosphocholines) with even-numbered chain lengths between 22 and 32 carbon atoms is described. Two new synthetic strategies for the preparation of long-chain 1,ω-diols as hydrocarbon building blocks are presented. The temperature-dependent self-assembly of the single-chain bolaamphiphiles was investigated by cryo transmission electron microscopy (cryo-TEM), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR).
Drescher, Simon,Meister, Annette,Blume, Alfred,Karlsson, Goeran,Almgren, Mats,Dobner, Bodo
p. 5300 - 5307
(2008/02/11)

Hydrogelation agents
A gelatinizer is provided having a component which promises to have biological compatibility, which can easily be mass-produced by a simple method, and which can solidify a large amount of water or aqueous solution when only a very small weight of it is used. This invention is a hydrogelatinizer represented by the general formula: R-An where A, which may be identical or different, are respectively nucleotides, n is 2 or 3, and R is a hydrocarbon chain (when n is 2, R is bivalent, and when n is 3, R is trivalent), said hydrocarbon being bonded to a phosphoric acid part of said nucleotides.
-
Page/Page column 3

(2008/06/13)

DERMATOLOGICAL COMPOSITIONS AND METHODS
Disclosed are methods and compositions for regulating the melanin content of mammalian melanocytes; regulating pigmentation in mammalian skin, hair, wool or fur; treating or preventing various skin and proliferative disorders; by administration of various compounds, including alcohols, diols and/or triols and their analogues.
-
(2008/06/13)

Treatment of neurodegenerative diseases
Disclosed are methods for increasing the differentiation of mammalian neuronal cells for purposes of treating neurodegenerative diseases or nerve damage by administration of various compounds including alcohols, diols and/or triols and their analogues.
-
(2008/06/13)

Treatment of diseases mediated by the nitric oxide/cGMP/protein kinase G pathway
Disclosed are methods and compositions for stimulating cellular nitric oxide (NO) synthesis, cyclic guanosine monophosphate levels (cGMP), and protein kinase G (PKG) activity for purposes of treating diseases mediated by deficiencies in the NO/cGMP/PKG signal transduction pathway, by administration of various compounds including alcohols, diols and/or triols and their analogues.
-
(2008/06/13)

Preparation of ω-hydroxy acids by reduction of α,ω-methylene diesters with NaBH4
By reaction of the dicesium salts of long chain dicarboxylic acids (C atoms > 9) with methylene iodide the corresponding methylene diesters were prepared. These acylals, by reduction with NaBH4 in THF, give the corresponding ω-hydroxy acids.
Benitez, Pilar,Delgado, Ana,Farrera, Joan-Anton,Ribo, Josep M.
p. 1697 - 1702
(2007/10/03)

Ruthenium hydrogenation catalysts
The invention relates to a novel ruthenium complex having the formula Ru(η3 -C6 H8 -PCy2)(PCy3)Cl, wherein Cy is cyclohexyl; its use in the preparation of RuHCl(H2)(PCy3)2 and RuH2 (H2)2 (PCy3)2 ; and the use of the complexes as catalysts in hydrogenation, imination and reductive hydrolysis processes.
-
(2008/06/13)

Multiple Electron Tunneling Paths across Self-Assembled Monolayers of Alkanethiols with Attached Ruthenium(II/III) Redox Centers
Alkanethiol monolayers with pendant redox centers are deposited on gold electrodes by selfassembly.The monolayers are composed of both an electroactive thiol, HS(CH2)nC(O)NHCH2pyRu(NH3)5(2+/3+), with 10-15 methylene groups, and a diluent thiol, HS(CH2)mCOOH, also with 10-15 methylene groups.The monolayers are classified as "matched" (n = m), "exposed" ( n = 15, m = 10-14), and "buried" (n = 10, m = 11-15) according to the relative position of the redox center.Cyclic voltammograms in aqueous Na2SO4 indicate that the monolayers are close-packed with the redox centers residing in the aqueous phase in all but the most buried cases.Measurements of electron transfer kinetics by several methods (cyclic voltammetry, ac impedance spectroscopy, chronoamperometry) yield an internally consistent set of kinetic parameters, the standard rate constant ko, and the reorganization energy λ of the redox centers.The reorganization energies are in good agreement with the theoretically predicted value of 1.0 eV for the pyRu(NH3)5 redox centers.Plots of ln(ko) vs m are linear in all three cases.The slopes of the linear regression fit provide tunneling parameters (β, where ko ca. e-βm) of 0.97 +/- 0.03 (matched cases), 0,83 +/- 0.03 (exposed cases) and 0.16 +/- 0.02 (buried cases) per methylene.This pattern of β's is interpreted in terms of electronic coupling between the redox center and the electrode via both the redox thiol and the proximate diluent thiols, with the coupling via the diluent thiols dominating in the exposed cases.
Finklea, Harry O.,Liu, Luna,Ravenscroft Melissa S.,Punturi, Sesto
p. 18852 - 18858
(2007/10/03)

Ytterbium(III) triflate-catalyzed selective methanolysis of methoxyacetates: A new deprotective method
-
Hanamoto, Takeshi,Sugimoto, Yuichi,Yokoyama, Yasuo,Inanaga, Junji
p. 4491 - 4492
(2007/10/03)

An Air-Stable Catalyst System for the Conversion of Esters to Alcohols
The combination of 5 mol percent of Ti(O-i-Pr)4 with 2.5-3.0 equiv (EtO)3SiH cleanly hydrosilylates esters to silyl ethers at 40-55 deg C, which can be converted to the corresponding primary alcohols via aqueous alkaline hydrolysis in excellent overall yield.The reaction can be carried out in the air, without solvent, and displays a high level of functional group compatibility.
Berk, Scott C.,Buchwald, Stephen L.
p. 3751 - 3753
(2007/10/02)

LOW-VALENT TITANIUM: A NEW APPROACH TO DEPROTECTION OF ALLYL AND BENZYL GROUPS
A novel method for the deprotection of allyl and benzyl derivatives of alcohols and phenols by low-valent titanium is reported.The possible mechanism is discussed.
Kadam, S. M.,Nayak, S. K.,Banerji, A.
p. 5129 - 5132
(2007/10/02)

Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. Strain energies and conformations
The enthalpies of hydrolysis of the monocyclic lactones from γ-butyrolactone to tridecanolactone were determined calorimetrically, and the acyclic ethyl having the number of atoms were studied in the fashion. The enthalpies of reduction of the lactones to the corresponding α,ω-alkanediols with lithium triethylborohydride also were determined. The enthalpies of formation of the lactones and the ethyl esters were derived from these data. They were converted to values for the gas phase by measuring the enthalpies of vaporization of ethyl esters and of lactones. In the of γ-butyrolactone and δ-valerolactone, the enthalpies of formation were in good accord with the previously reported values determined via combustion calorimetry. The strain energies of the lactones were obtained via isodesmic reactions. Valerolactone had a strain energy of 11 kcal/mol, and the largest strain energy was found with octanolactone (13 kcal/mol). The conformations of γ-butyrolactone and δ-valerolactone were studied via MP2/6-31G* geometry optimizations, and the conformations of the other lactones were studied with use of the molecular mechanics program MM3. The energies of the lactones estimated via molecular mechanics were compared with the experimental results.
Wiberg, Kenneth B.,Waldron, Roy F.
p. 7697 - 7705
(2007/10/02)

Polyetherimide bisphenol compositions
Polyetherimide bisphenols and bischloroformates are prepared by the reaction of dianhydrides or certain bisimides with aminophenols or mixtures thereof with diamines. They are useful as intermediates for the preparation of cyclic heterocarbonates, which may in turn be converted to linear copolycarbonates. The bisphenols can also be converted to salts which react with cyclic polycarbonate oligomers to form block copolyetherimidecarbonates.
-
(2008/06/13)

Long Chain Phenols. Part 19. The Synthesis of 3-phenol, 'Cardanol Monoene', and of 3-phenol, 'Cardanol Diene', and their Methyl Ethers
-
Caplin, Joseph,Tyman, John H. P.
p. 321 - 351
(2007/10/02)

Synthesis of 14-hydroxytetra- and 15-hydroxypentadecanoic acids
14-Hydroxytetradecanoic and 15-hydroxypentadecanoic acids were synthesized from 1,10-decanedicarboxylic and 1,11-undecanedicarboxylic acids.The diesters of the latter were reduced to the diols, from which the chlorohydrins were obtained by reaction with hydrogen chloride.The use of these chlorohydrins in the sodiomalonic synthesis leads to the hydroxy carboxylic acids.
Zakharkin, L. I.,Guseva V. V.,Pryanishnikov A. P.
p. 658 - 661
(2007/10/02)