- Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols
-
A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.
- Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji
-
supporting information
p. 20394 - 20398
(2020/09/21)
-
- Cytotoxic linear acetylenes from a marine sponge Pleroma sp.
-
Bioassay-guided fractionation of the extract of the rare deep-sea marine sponge Pleroma sp. afforded seven new linear acetylenes, yakushynols A-F (1-6) and neopetroformyne E (7). The structures of 1-7 were determined by a combination of the analysis of spectroscopic data and chemical derivatization. Compounds 1-6 are the first examples of the sponge-derived acetylenes of the size of duryne with oxidation at the sixth carbon from the terminus. Compounds 1-5 and 7 exhibited moderate cytotoxic activity. A biosynthetic route of neopetroformyne A was inferred from the structural transition among sponge-derived linear acetylenes.
- Takanashi, Emi,Takada, Kentaro,Hashimoto, Masahiro,Itoh, Yoshiyuki,Ise, Yuji,Ohtsuka, Susumu,Okada, Shigeru,Matsunaga, Shigeki
-
p. 9564 - 9570
(2015/12/01)
-
- Addition of carboxyalkyl radicals to alkenes through a catalytic process, using a Mn(II)/Co(II)/O2 redox system
-
A novel strategy for production of mono- and dicarboxylic acids by the addition of carboxyalkyl radicals to alkenes and dienes, respectively, was successfully developed through a catalytic process with use of Mn(II)/Co(II)/O2 system. Thus, a variety of carboxylic acids were prepared by the reaction of alkenes and dienes with acid anhydrides in the presence of a very small amount of Mn(OAc)2 (0.5 mol %) and Co(OAc)2 (0.1 mol %) under dilute dioxygen.
- Hirase, Koji,Sakaguchi, Satoshi,Ishii, Yasutaka
-
p. 5974 - 5976
(2007/10/03)
-
- cis/trans-Ozonides of Cycloolefins
-
Ozonolyses in pentane of the unsubstituted cycloolefins having eleven-, twelve-, fourteen- and sixteen-membered rings (1b-e) and of cyclohexadecen-8-one (12) gave the corresponding cis- (2b-e; cis-15a) and trans-ozonides (3b-e; trans-15a), whereas cyclodecene (1a) gave only the corresponding cis-ozonide (2a).Ozonolyses on polyethylene of the dimethyl-substituted cycloolefins bearing fourteen- and sixteen-membered rings (7b,c) also afforded cis- and trans-isomeric ozonides (8, 9), whereas from the twelve-membered ring (7a) only the corresponding cis-ozonide (8a) was formed. - Keywords: Ozonides; Cycloolefins
- Griesbaum, Karl,Ball, Volker,Beck, Johannes,McCullough, Kevin
-
p. 1993 - 2000
(2007/10/03)
-
- Bifunctional compounds from reaction of alkoxy hydroperoxides with metal salts
-
Alkoxy hydroperoxides, obtained by ozonizing olefins in alcoholic solution, were treated with ferrous sulfate. C-C bond scission and radical formation was followed by dimerization of the radicals formed. Ozonides reacted similarly. Acyclic and cyclic olefins, including a cyclic enol ether, gave rise to a range of α,ω-disubstituted products in modest yields. By using ferric chloride, ω-chloro esters were obtained from the alkoxy hydroperoxides derived from olefinic esters.
- Cardinale,Laan,Van Der Steen,Ward
-
p. 6051 - 6054
(2007/10/02)
-
- One-step Synthesis of Long-chain Aliphatic α,ω-Dicarboxylic Acids Utilizing the Copper-catalyzed Reaction of β-Propiolactone with α,ω-Di-Grignard Reagents
-
Copper-catalyzed reaction of β-propiolactone with α,ω-di-Grignard reagents, followed by esterification gave six-carbon homologated α,ω-dicarboxylic acid esters in good yields.
- Fujisawa, Tamotsu,Sato, Toshio,Kawara, Tatsuo,Tago, Hideyuki
-
p. 345 - 346
(2007/10/02)
-
- 2,2':5',2''-Terthiophene-5-carboxylic Acid and 2,2':5',2''-Terthiophene-5,5''-dicarboxylic Acid
-
2,2':5',2''-Terthiophene-5-carboxylic acid was obtained in excellent yield by treating 2,2':5',2''-terthiophene with lithium diisopropylamide, followed by carboxylation of the lithium salt with solid carbon dioxide.The 5,5''-dicarboxylic acid was obtained similarly, when 2 equiv of base were used.Attempted syntheses of the monoacid, based on the oxidation of the corresponding aldehyde or the acetyl derivative, were unsuccessful.Both the monoacid and the 5,5'-diacid sensitized the hemolysis of human erythrocytes in the presence of ultraviolet light.
- Kagan, Jacques,Arora, Sudershan K.,Uestuenol, Ayse
-
p. 4076 - 4078
(2007/10/02)
-
- Kolbe Synthesis of Unsaturated Pheromones by Coelectrolysis with 5-Alkynoic Acids
-
The alkynoic acids 5a - g are synthesized by coelectrolysis of 5-alkynoic acids 2a - c with dicarboxylic monoesters 3a - d.By reduction, Lindlar-hydrogenation, and acetylation these are converted into pheromones such as (Z)-11-hexadecenyl acetate (7b), the pheromone of Mamestra brassicae. 2a - c can be prepared by alkynylation of 1-bromo-3-chloropropane to 1a - c, substitution by cyanide and hydrolysis.
- Seidel, Wolfgang,Schaefer, Hans J.
-
p. 3898 - 3903
(2007/10/02)
-