cas 13019-22-2, 9-Decen-1-ol | Articles data

Articles about 13019-22-2Total 38 be found

Article title
Article abstract
Author
Journal number and time
Download

A Selective Monodehydration of C4-14-α,ω-Alkanediols with Stearic and/or Palmitic Acids
The formation of monoesters of the C4-14-α,ω-alkanediol (1) with stearic and/or palmitic acids and the consecutive pyrolysis of the monoesters to an ω-alken-1-ol (2) were effected at 320-350 deg C under 260-760 mmHg in a backmix flow reactor of a constant volume equipped with a fractionating column, through which the unchanged 1 was partially recycled.The selectivity in the preparations of 2(C6, C10, C14) was greater than 79percent.
Yamanaka, Tohr,Imai, Takashi
p. 1585 - 1586
(1981)
Read Online

An optimized process to 10-bromo-1-decanol
A multivariate design and optimization study for the synthesis of the bromoalkanol 10-bromo-1-decanol using decane-1,10-diol as substrate is reported. The bromination process was supported by the phase transfer catalyst tetrabutylammonium bromide with aqueous HBr (48%) as the brominating reagent. The optimized batch protocol provided a yield of 64% of 10-bromo-1-decanol 2 TM with a conversion of 80%, and 10% of the dibrominated alkane 1,10-dibromodecane 3, a characteristic byproduct, was formed.
Spaccini, Raffaele,Tsoukala, Anna,Liguori, Lucia,Punta, Carlo,Borsvik, Hans-Rene
p. 1215 - 1220
(2010)
Read Online

Concise syntheses of insect pheromones using Z-Selective cross metathesis
Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.
Herbert, Myles B.,Marx, Vanessa M.,Pederson, Richard L.,Grubbs, Robert H.
p. 310 - 314
(2013)
Read Online

Regiodivergent Reductive Opening of Epoxides by Catalytic Hydrogenation Promoted by a (Cyclopentadienone)iron Complex
The reductive opening of epoxides represents an attractive method for the synthesis of alcohols, but its potential application is limited by the use of stoichiometric amounts of metal hydride reducing agents (e.g., LiAlH4). For this reason, the corresponding homogeneous catalytic version with H2 is receiving increasing attention. However, investigation of this alternative has just begun, and several issues are still present, such as the use of noble metals/expensive ligands, high catalytic loading, and poor regioselectivity. Herein, we describe the use of a cheap and easy-To-handle (cyclopentadienone)iron complex (1a), previously developed by some of us, as a precatalyst for the reductive opening of epoxides with H2. While aryl epoxides smoothly reacted to afford linear alcohols, aliphatic epoxides turned out to be particularly challenging, requiring the presence of a Lewis acid cocatalyst. Remarkably, we found that it is possible to steer the regioselectivity with a careful choice of Lewis acid. A series of deuterium labeling and computational studies were run to investigate the reaction mechanism, which seems to involve more than a single pathway.
De Vries, Johannes G.,Gandini, Tommaso,Gennari, Cesare,Jiao, Haijun,Pignataro, Luca,Stadler, Bernhard M.,Tadiello, Laura,Tin, Sergey
p. 235 - 246
(2022/01/03)

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides
The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.
Lambert, Tristan H.,Steiniger, Keri A.
supporting information
p. 8013 - 8017
(2021/10/25)

CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF
The present application discloses a compound of formula (I) or a salt thereof: (I) and compositions comprising such compound or salt thereof. The use of such compound, salt thereof or composition comprising same for treating anemia or leukopenia, fibrosis, cancer, hypertension and/or a metabolic condition in a subject is also disclosed.
-
Page/Page column 47; 69; 80

(2021/06/26)

Chemoselective Electrosynthesis Using Rapid Alternating Polarity
Challenges in the selective manipulation of functional groups (chemoselectivity) in organic synthesis have historically been overcome either by using reagents/catalysts that tunably interact with a substrate or through modification to shield undesired sites of reactivity (protecting groups). Although electrochemistry offers precise redox control to achieve unique chemoselectivity, this approach often becomes challenging in the presence of multiple redox-active functionalities. Historically, electrosynthesis has been performed almost solely by using direct current (DC). In contrast, applying alternating current (AC) has been known to change reaction outcomes considerably on an analytical scale but has rarely been strategically exploited for use in complex preparative organic synthesis. Here we show how a square waveform employed to deliver electric current - rapid alternating polarity (rAP) - enables control over reaction outcomes in the chemoselective reduction of carbonyl compounds, one of the most widely used reaction manifolds. The reactivity observed cannot be recapitulated using DC electrolysis or chemical reagents. The synthetic value brought by this new method for controlling chemoselectivity is vividly demonstrated in the context of classical reactivity problems such as chiral auxiliary removal and cutting-edge medicinal chemistry topics such as the synthesis of PROTACs.
Baran, Phil S.,Carlson, Ethan,Edwards, Jacob T.,Hayashi, Kyohei,Kawamata, Yu,Saito, Masato,Shaji, Shobin,Simmons, Bryan J.,Waldmann, Dirk,Zapf, Christoph W.
p. 16580 - 16588
(2021/10/20)

Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles
Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a green protic solvent. This environmentally friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the completion of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation was presented, which allows minimization of chemical waste production.
Grela, Karol,Kusy, Rafa?
supporting information
p. 5494 - 5502
(2021/08/16)

Chemoselective Oxidation of p-Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst
The oxidation of p-methoxy benzyl (PMB) ethers was achieved using nitroxyl radical catalyst 1, which contains electron-withdrawing ester groups adjacent to the nitroxyl group. The oxidative deprotection of the PMB moieties on the hydroxy groups was observed upon treatment of 1 with 1 equiv of the co-oxidant phenyl iodonium bis(trifluoroacetate) (PIFA). The corresponding carbonyl compounds were obtained by treating the PMB-protected alcohols with 1 and an excess of PIFA.
Hamada, Shohei,Sugimoto, Koichi,Elboray, Elghareeb E.,Kawabata, Takeo,Furuta, Takumi
supporting information
p. 5486 - 5490
(2020/07/24)

CREATINE PRODRUGS, COMPOSITIONS AND METHODS OF USE THEREOF
The present disclosure provides creatine prodrug analogs and their compositions useful for the treatment of creatine deficiencies.
-
Paragraph 00740-00741

(2019/06/17)

Oxidative Deprotection of p-Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis
An efficient and greener deprotection method for p-methoxybenzyl (PMB) ethers using a metal-free visible light photoredox catalyst and air and ammonium persulfate as the terminal oxidants is presented. Various functional groups and protecting groups were tolerated in the developed method to achieve good to excellent yields in short reaction times. Significantly, the developed method was compatible with PMB ethers derived from primary, secondary, and tertiary alcohols and a gram-scale reaction. Mechanistic studies support a proposed reaction mechanism that involves single electron oxidation of the PMB ether.
Ahn, Deok Kyun,Kang, Young Woo,Woo, Sang Kook
p. 3612 - 3623
(2019/03/11)

Sequential Alkene Isomerization and Ring-Closing Metathesis in Production of Macrocyclic Musks from Biomass
We report successful utilization of sequential alkene isomerization and ring-closing metathesis of dec-9-enoic acid based dienes in synthesis of macrocyclic lactones that possess a strong scent of musk. This catalytic sequence was essential to trim the chain length of starting dienes to yield macrocycles of the right size. Dec-9-enoic acid is conveniently obtainable from oleic esters by Ru-catalysed ethenolysis.
Sytniczuk, Adrian,Forcher, Gwéna?l,Grotjahn, Douglas B.,Grela, Karol
supporting information
p. 10403 - 10408
(2018/07/31)

Rhenium-catalyzed deoxydehydration of renewable triols derived from sugars
An efficient method for the catalytic deoxydehydration of renewable triols, including those obtained from 5-HMF, is described. The corresponding unsaturated alcohols were obtained in good yields using simple rhenium(vii)oxide under neat conditions and ambient atmosphere at 165 °C.
Wozniak, Bartosz,Li, Yuehui,Tin, Sergey,De Vries, Johannes G.
supporting information
p. 4433 - 4437
(2018/10/17)

PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS
In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.
-
Paragraph 0397

(2017/06/12)

Synthesis method for 9-decenol
The invention discloses a synthesis method for 9-decenol. The synthesis method includes the following steps that 1,10-decanediol, higher fatty acid and a catalyst are stirred, mixed and heated to 340-360 DEG C, and a mixed matrix is obtained; 1,10-decanediol is continuously fed into the mixed matrix with the temperature maintained at 340-360 DEG C in a dropwise adding mode, and continuous discharging is achieved in a rectification mode; an obtained discharged material is subjected to normal-pressure rectification, and 99+/-0.5 DEG C fraction is collected; remaining materials are subjected to vacuum rectification, 110+/-0.5 DEG C/30 mm Hg fraction is collected, and 9-decenol is obtained; 1,10-decanediol is mixed into kettle bottom liquid obtained after vacuum rectification, an obtained mixture replaces 1,10-decanediol for continuous feeding, and a circular reaction can be continuously performed.
-
Paragraph 0035 - 0038

(2017/01/12)

UNSATURATED FATTY ALCOHOL DERIVATIVES FROM NATURAL OIL METATHESIS
Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.
-
Paragraph 0093; 0094; 0095

(2015/03/31)

HYDROGENATION OF ESTERS WITH FE/TRIDENTATE LIGANDS COMPLEXES
The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of Fe complexes with tridentate ligands, having one amino or imino coordinating group and two phosphino coordinating groups, in hydrogenation processes for the reduction of ketones, aldehydes, esters or lactones into the corresponding alcohol or diol, respectively.
-
Page/Page column 21; 22

(2015/07/07)

PROCESS FOR THE CHEMOSELECTIVE REDUCTION OF TERMINALLY SATURATED CARBOXYLIC ESTERS
The chemoselective reduction of a carboxylic ester (I) to an alcohol by catalytic hydrogenation, in particular in the presence of a transition metal complex, more particularly in the presence of a ruthenium (II) complex is described.
-
Paragraph 0071-0073

(2015/06/10)

ALKENYL GLYCOSIDES AND THEIR PREPARATION
An alkenyl glycoside is prepared by reacting a metathesis-derived unsaturated fatty alcohol containing 10 to 30 carbon atoms with either (1) a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide, or (2) a hydrocarbyl glycoside produced by reacting an alcohol containing up to 6 carbon atoms with a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide. Each of these reactions is performed in the presence of an acid catalyst and under conditions sufficient to form the alkenyl glycoside or hydrocarbyl glycoside. The preferred alkenyl glycosides are 9-decen-1-yl glycoside; 9-dodecen-1-yl glycoside; 9-tridecen-1-yl glycoside; 9-pentadecen-1-yl glycoside; 9-octadecen-yl glycoside; or 9-octadecen-1,18-diyl glycoside.
-
Paragraph 0080

(2014/09/30)

UNSATURATED FATTY ALCOHOL COMPOSITIONS AND DERIVATIVES FROM NATURAL OIL METATHESIS
Unsaturated alcohol compositions are obtained by reducing a metathesis-derived hydrocarbyl unsaturated ester. Also disclosed is a process for preparing an unsaturated alcohol composition, where a metathesis derived hydrocarbyl carbonyl compound is reacted in the presence of a silane compound, an organic solvent, and a catalyst system prepared from a metallic complex and a reducing agent. This mixture is then hydrolyzed with a metallic base, and then mixed with organic solvent. The resultant mixture is then separated, washed, dried, and/or purified to produce the unsaturated alcohol composition. The unsaturated alcohol derivatives are useful in many end-use applications, including, for example, lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, plasticizers, asphalt additives, friction reducing agents, plastics, and adhesives.
-
Paragraph 0068; 0069; 0070

(2013/11/05)

PROCESS FOR THE CHEMOSELECTIVE REDUCTION OF TERMINALLY SATURATED CARBOXYLIC ESTERS
The chemoselective reduction of a carboxylic ester (I) to an alcohol by catalytic hydrogenation, in particular in the presence of a transition metal complex, more particularly in the presence of a ruthenium (II) complex is described.
-
Page/Page column 15-16

(2013/12/03)

Synthetic route discovery and introductory optimization of a novel process to idebenone
An environmentally benign, convenient, high yielding, and cost-effective synthesis leading to idebenone is disclosed. The synthesis includes a bromination process for the preparation of 2-bromo-3,4,5-trimethoxy-1- methylbenzene, a protocol for the Heck cross-coupling reaction using either thermal or microwave heating, olefin reduction by palladium catalyzed hydrogenation, and a green oxidation protocol with hydrogen peroxide as oxidant to achieve the benzoquinone framework. The total synthesis is composed of six steps that provide an overall yield of 20% that corresponds to a step yield of 76%.
Tsoukala, Anna,Bjorsvik, Hans-Rene
experimental part
p. 673 - 680
(2011/12/01)

Vapor-phase catalytic dehydration of terminal diols
Vapor-phase catalytic reactions of several terminal diols were investigated over several rare earth oxides, such as Sc2O3, Y 2O3, CeO2, Yb2O3, and Lu2O3. Sc2O3 showed selective catalytic activity in the dehydration of terminal diols with long carbon chain, such as 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, and 1,12-dodecanediol, to produce the corresponding unsaturated alcohols. In the dehydration of 1,6-hexanediol, 5-hexen-1-ol was produced with selectivity over 60 mol%, together with by-products such as ε-caprolactone and oxacycloheptane. In the dehydration of 1,10-decanediol, 9-decen-1-ol was produced with selectivity higher than 70 mol%. In addition to Sc 2O3, heavy rare earth oxides such as Lu2O 3 as well as monoclinic ZrO2 showed moderate selectivity in the dehydration of the terminal diols.
Abe, Katsutoshi,Ohishi, Yusuke,Okada, Takuto,Yamada, Yasuhiro,Sato, Satoshi
experimental part
p. 419 - 424
(2012/02/03)

Mn(0)-mediated chemoselective reduction of aldehydes. Application to the synthesis of α-deuterioalcohols
A mild, simple, safe, chemoselective reduction of different kinds of aldehydes to the corresponding alcohols mediated by the Mn dust/water system is described. In addition to this, the use of D2O leads to the synthesis of α-deuterated alcohols and constitutes an efficient, inexpensive alternative for the preparation of these compounds.
Jimenez, Tania,Barea, Elisa,Oltra, J. Enrique,Cuerva, Juan M.,Justicia, Jose
experimental part
p. 7022 - 7025
(2010/11/18)

Cleavage of benzyl ethers by triphenylphosphine hydrobromide
Triphenylphosphine hydrobromide was found to cleave the benzyl ethers derived from 1°, 2° alkyl, and aryl alcohols to the corresponding alcohols and benzyltriphenylphosphonium bromide in good yields. Alkene and allyl phosphonium salts were produced from the benzyl ethers with 3° alkyl and allyl groups, respectively. These results indicate that the formation of the product is determined by the relative stability of the carbocationic intermediate. The anhydrous, stoichiometric amount of PPh3·HBr offers a new and effective method for the deprotection of benzyl ethers.
Ramanathan, Mani,Hou, Duen-Ren
supporting information; experimental part
p. 6143 - 6145
(2010/12/24)

Deprotection of benzyl ethers using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under photoirradiation
The deprotection of benzyl ethers was effectively realized in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in MeCN under photoirradiation using a long wavelength UV light.
Rahim, Mohammad Abdur,Matsumura, Shuichi,Toshima, Kazunobu
p. 7307 - 7309
(2007/10/03)

Compounds having protected hydroxy groups
The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
-
(2008/06/13)

Ketone precursors for organoleptic compounds
The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.
-
(2008/06/13)

A novel hydrogen transfer hydroalumination of alkenes with triisobutylaluminum catalyzed by Pd and other late transition metal complexes
Hydrogen transfer hydroalumination of terminal alkenes and dienes can be achieved with 1.1 equiv. of (i-Bu)3Al and catalytic amounts of Cl2Pd(PPh3)2 and other late transition metal complexes containing Co, Rh, Ni, and Pt at ambient temperature in high yields.
Gagneur, Sebastien,Makabe, Hidefumi,Negishi, Ei-Ichi
p. 785 - 787
(2007/10/03)

Novel and facile selective reduction of carboxylic acid with a samarium diiodide-lanthanide triflate-methanol-base system
The facile selective reduction of carboxylic acids in the presence of an aldehyde or that bearing a formyl group proceeded smoothly with a samarium diiodide-lanthanide triflate-methanol-base system at room temperature to give the corresponding alcohols in good to almost quantitative yield.
Kamochi, Yasuko,Kudo, Tadahiro
p. 341 - 344
(2007/10/03)

CuCl2.2H2O MeOH. A new reagent system for the deprotection of tetrahydropyranyl ethers
Cupric chloride dihydrate in methanol cleave the tetrahydropyranyl ethers to the corresponding alcohols in excellent yields under mild conditions.
Davis, K. Joju,Bhalerao,Vittal Rao
p. 2301 - 2308
(2007/10/03)

Hydrogen transfer hydrozirconation of alkenes with iBuZrCp2Cl catalyzed by Lewis-acidic metal compounds containing Al, Zn, Si, Ag, and Pd
The hydrozirconation reaction of monosubstituted alkenes with iBuZrCp2Cl can be significantly accelerated by catalytic amounts of various Lewis acidic metal compounds, most notably AlCl3, Me3SiI, and Pd complexes, such as Li2PdCl4 and Cl2Pd(PPh3)2.
Makabe, Hidefumi,Negishi, Ei-Ichi
p. 969 - 971
(2007/10/03)

Electroorganic synthesis 65. Anodic homocoupling of carboxylic acids derived from fatty acids
Fatty acid derived carboxylic acids with double bonds, hydroxy-, amino-, keto-, ester- and epoxy groups are anodically coupled to dimers (Kolbe electrolysis) in 29 to 81% yield and up to a 2.5 mol scale. Problems due to the low conductivity of fatty acid salts were overcome by the use of a flow cell with a narrow electrode gap. Fatty acids with branched alkyl chains gave dimers with interesting emulsifying properties. Dimethyl hexadecanedioate, accessible from methyl azelate, could be cyclized and further converted into homomuscone and muscone in a few steps. A commercial mixture of dimeric fatty acids (C36-dicarboxylic acids) has been coupled to give C70-diesters. Acta Chemica Scandinavica 1998. Part 64: Nielsen, M. F., Batanero, B.,.
Weiper-Idelmann, Andreas,Aus Dem Kahmen, Martin,Schaefer, Hans J.,Gockeln, Marianne
p. 672 - 682
(2007/10/03)

Ester/alcohol synthesis
A process for preparing an ester of the formula, , R1-O-CO-R2 , , wherein R1 is an alkenyl group and R2 is an alkyl, alkenyl or alkynyl group, which comprises reacting the corresponding halide of formula R1Hal with the corresponding alkali metal acylate of the formula MOCOR2, in the presence of an inert aprotic solvent and a phase-transfer catalyst, optionally followed by hydrolysis of the ester into the corresponding alcohol.
-
(2008/06/13)

ALKENYL COPPER REAGENTS-26 CARBOCUPRATION OF ALKYNES BY ORGANOCOPPER REAGENTS BEARING A PROTECTED HYDROXY OR THIOL FUNCTION
Halohydrins, protected as ethers, acetals or chloro-magnesium alcoholates are sequentially transformed into the Li or Mg reagents and then into copper or cuprate derivatives.Addition to acetylene or propyne is discussed according to various parameters.The alkenyl copper or cuprate species, thus obtained, may react further with various electrophiles, leading to difunctionalized alkenes.
Gardette, M.,Alexakis, A.,Normant, J. F.
p. 5887 - 5900
(2007/10/02)

Ate Complex from Diisobutylaluminum Hydride and n-Butyllithium as a Powerful and Selective Reducing Agent for the Reduction of Selected Organic Compounds Containing Various Functional Groups
The "ate" complex generated from diisobutylaluminum hydride and n-butyllithium in an equimolar ratio either in tetrahydrofuran-hexane or in toluene-hexane was reacted with a series of selected organic compounds containing various functional groups in order to explore the reducing properties and to determine the synthetic utility of the reagent.The reagent is very effective for selective 1,2-reduction of both acyclic and cyclic enones.The reagent in tetrahydrofuran-hexane gives slightly better 1,2-selectivity than in toluene-hexane in the reduction of some acyclic enones, whereas the reagent in toluene-hexane gives better 1,2-selectivity in the reduction of conjugated cyclohexenones.Esters and lactones are completely reduced to the corresponding alcohols at room temperature, whereas they are reduced to the corresponding alcohols and aldehydes at -78 deg C even with an excess amount of the reagent.Partial reduction of the esters and the lactones to the corresponding aldehydes has not been observed.Acid chlorides are rapidly reduced to the corresponding alcohols with an excess amount of the reagent at -78 deg C, whereas they are reduced to a mixture of the alcohol, the aldehyde, and the unreacted acid chloride with a stoichiometric amount of the reagent at -78 deg C.Acid anhydrides are rapidly and quantitatively reduced to an equimolar mixture of the acid and the alcohol at -78 deg C.Carboxylic acids and primary and secondary amides are inert to the reagent at room temperature and are recovered unchanged..Tertiary amides are cleanly reduced to the aldehydes with a stoichiometric amount of the reagent either at 0 deg C or at room temperature, whereas they are inert to the reagent at -78 deg C, which permits the selective reduction of other reducible functional groups in the presence of the tertiary amide group at the latter temperature.The reagent rapidly reduces simple primary alkyl, benzyl, and allyl bromides but slowly primary alkyl chlorides and secondary alkyl bromides.Tertiary alkyl and aryl halides are essentially inert to the reagent, whereas trityl bromide and vinyl bromide are reduced at a reasonable rate.Epoxides are cleanly reduced to the corresponding alcohols.The opening of the epoxide ring with this reagent proceeds with excellent isomeric purity, yielding the more highly substituted alcohol almost exclusively.Nitriles are resistant to reduction and are only slowly converted to the corresponding aldehydes at room temperature.Disulfides are rapidly and quantitatively reduced to the corresponding thiols.Sulfoxides and sulfones are inert to the reagent and are recovered unchanged.Selective reductions of an ester in the presence of other reducible groups such as a bromide, a tertiary amide, and a nitrile are achieved with the reagent at -78 deg C by using a modified procedure.Furthermore, the reagent is capable of reducing selectively a ketone in the presence of an ester.
Kim, Sunggak,Ahn, Kyo Han
p. 1717 - 1724
(2007/10/02)

Production of ω-alkene-1-ols
A process for producing ω-alkene-1-ols which comprises reacting an α,ω-alkanediol having 4 to 14 carbon atoms with a fatty acid selected from the group consisting of stearic acid, palmitic acid and a mixture of stearic acid and palmitic acid.
-
(2008/06/13)