13139-94-1Relevant articles and documents
Dibromomethane as one-carbon source in organic synthesis: A versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes
Hon, Yung-Son,Liu, Yu-Wei,Hsieh, Cheng-Han
, p. 4837 - 4860 (2007/10/03)
Ozonolysis of mono-substituted alkenes A-1 followed by reacting with a preheated mixture of CH2Br2-Et2NH affords α-substituted acroleins A-2 in good yields. Under very mild reaction conditions, these α-substituted acroleins A-2 can be easily converted to α-methylene esters A-4, which could be further converted to the corresponding α-keto esters A-5. This methodology can be also applied to the preparation of α-methylene lactones B-4, α-methylene lactams, and α-keto lactones B-5 with various ring sizes.
Oxidation of Alkynes by Hydrogen Peroxide Catalyzed by Methylrhenium Trioxide
Zhu, Zuolin,Espenson, James H.
, p. 7728 - 7732 (2007/10/03)
The oxidation of alkynes with hydrogen peroxide is catalyzed by methylrhenium tioxide.The reactions can be rationalized by postulating that an oxirene intermediate is formed between a rhenium peroxide and the alkyne.Internal alkynes yield α-diketones and carboxylic acids, the latter from the complete cleavage of the triple bonds.Rearrangement products were observed only for aliphatic alkynes.Terminal alkynes gave carboxylic acids and their derivatives and α-keto acids as the major products, but their yields varied with the solvent used.
REACTIONS OF N,O-BIS(BROMOMAGNESIO) α-HYDROXY CARBOXAMIDES WITH CHLOROFORMIC ESTERS
Zul'karnaev, R. I.,Fedotov, A. S.,Lapkin, I. I.
, p. 316 - 321 (2007/10/02)
In the reactions of N,O-bis(bromomagnesio) α-hydroxy α-alkoxy carboxamides of the aliphatic series with chloroformic esters in boiling toluene unsaturated compounds are formed.Analogous reactions conducted at a higher temperature (boiling mesitylene) lead to the formation of reduced products.These reactions with ethyl chloroformate are faster and go with higher yields of the target product than the corresponding reactions with benzyl chloroformate.
SYNTHETIC METHODS BASED ON HALOGENOMAGNESIUM ALCOHOLATES. X. REACTIONS OF LITHIUM AND HALOGENOMAGNESIUM ALCOHOLATES WITH CHLORINATED ETHERS
Kashinskii, V. N.,Demanov, V. A.,Lapkin, I.I.
, p. 72 - 75 (2007/10/02)
The reaction of α-chlorinated ethers with lithium and halogenomagnesium alcoholates were investigated.Depending on the character of the radicals contained in the alcoholates, either alkoxymethyl derivatives of the enolic form of α-keto esters or the same derivatives of α-hydroxy esters are formed.
SYNTHETIC METHODS BASED ON HALOGENOMAGNESIUM ALCOHOLATES. XI. REACTION OF HALOGENOMAGNESIUM ALCOHOLATES WITH α-CHLORINATED THIOESTERS
Kashinskii, V. N.,Zul'karnaev, R. I.,Lapkin, I. I.
, p. 1420 - 1422 (2007/10/02)
A method is developed for the synthesis of esters of α-alkoxy-α-(alkylthiomethoxy)acids, based on the reaction of alkylmagnesium bromides with dialkyl oxalates with the subsequent action of α-chlorinated sulfides on the obtained bromomagnesium alcoholates of the α-alkoxy-α-hydroxy esters.
