7081-78-9Relevant articles and documents
Simple, rapid procedure for the synthesis of chloromethyl methyl ether and other chloro alkyl ethers
Berliner, Martin A.,Belecki, Katherine
, p. 9618 - 9621 (2007/10/03)
Zinc(II) salts catalyze the reaction between acetals and acid halides to provide haloalkyl ethers in near-quantitative yield. Reactions from millimole to mole scale are typically complete in 1-4 h with 0.01 mol % catalyst. The solutions of haloalkyl ethers thus obtained can be utilized directly in reactions in which the presence of the ester byproduct does not interfere. Excess haloalkyl ether is destroyed on workup, thereby minimizing exposure to this class of carcinogenic compounds.
Electrophilic Reactions of Activated Alkenes and Alkynes with Element Halides. III. Reaction of Activated Alkenes with Phosphorus Trihalides
Kazankova,Trostyanskaya,Efimova,Beletskaya
, p. 1606 - 1619 (2007/10/03)
Electrophilic substitution of the vinyl hydrogen atom in alkenyl alkyl ethers, 2-bromoethenyl alkyl ethers, and ketene acetals readily occurs under the action of phosphorus trihalides in the presence of an organic base to yield 70-98% of 2-alkoxy-, 2-alkoxy-1-bromo-, and 2,2-dialkoxyalkenylphosphonous dichlorides and dibromides. The reaction is regio- and stereospecific. A mechanism involving intermediate formation of a cyclic phosphiranium ion is proposed.
Electrophilic Reactions of Carbonyl Compounds and Their Derivatives. IX. Reactions of 3,4-Dimethoxyphenylacetone with Heterocarbenium Ions To Form 2-Benzopyrylium Salts
Luk'yanov, S. M.
, p. 927 - 933 (2007/10/03)
Reactions of 3,4-dimethoxyphenylacetone with a series of carbonyl compounds and their derivatives (benzaldehyde, α-chloroesters, vinyl ethyl ether, and geminal chlorohydrocarbons) as sources of heterocarbenium ions under conditions of acid catalysis and also with heterocarbenium salts yield 2-benzopyrylium salts.
Synthesis and antibiotic activity of 1-cycloalkoxymethyl-4-dimethylaminopyridinium and 1-[(1-alkoxy)ethyl]-4-dimethylaminopyridinium chlorides
Pernak,Michalak,Krysinski,Kuncewicz
, p. 531 - 533 (2007/10/02)
DMAP reacts readily with chloromethylcycloalkyl ethers and α-chloroethyl alkyl ethers to give stable (1a-1e) and unstable (2a-2b) pyridinium chlorides. Reaction of these chlorides with NaOH produces the corresponding 4-pyridones. All the chlorides synthesized showed antibiotic activity. Particularly high activity against microbes representing cocci, rods, fungi, and bacilli was shown by 1-cyclododecyloxymethyl-4-dimethylaminopyridinium chloride 1d and 1-[(1-dodecyloxy)ethyl]-4-dimethylaminopyridinium chloride 2f.
REACTIONS OF ISOCYANIDES. II- ADDITION TO ACETALS
Pellissier, Helene,Meou, Alain,Gil, Gerard
, p. 3505 - 3506 (2007/10/02)
In the presence of TiCl4, tert-butyl isocyanide reacts with aldehyde acetals to afford β-alkoxycyanoenamines.
REACTIONS OF ISOCYANIDES. II - ADDITION TO ACETALS
Pellissier, Helene,Meou, Alain,Gil, Gerard
, p. 2979 - 2980 (2007/10/02)
In the presence of TiCl4, tert-butyl isocyanide reacts with aldehyde acetals to afford β-alkoxycyanoenamines.
13C NMR Chemical Shifts - a Conformational Probe for 1-Alkoxyalkyl Esters
Pihlaja, Kalevi,Lampi, Aija
, p. 196 - 199 (2007/10/02)
Eighteen 1-alkoxyalkyl formates, acetates and propionates, , have been analysed by 13C NMR spectroscopy.When the chain length of R1, R2 or R3 increases, the 13C NMR resonances of C1, C2 and C3, respectively, shift to lower field.In addition to the primary substituent effects there are a few but minor interactive influences which, however, are clearly significant.All of these effects can be used to predict the most favoured conformation of the 1-alkoxyalkyl esters.
MECHANISMS FOR THE SOLVOLYTIC DECOMPOSITIONS OF NUCLEOSIDE ANALOGUES-I. ACIDIC HYDROLYSIS OF 2-SUBSTITUTED 1-(1-ETHOXYETHYL)BENZIMIDAZOLES
Loennberg, Harri,Kaeppi, Rainer
, p. 913 - 918 (2007/10/02)
A few 2-substituted 1-(1-ethoxyethyl)benzimidazoles have been prepared and the rate constants for their hydrolysis measured at various temperatures and oxonium ion concentrations.The formal kinetics followed and the effect of varying the 2-substitution on the hydrolysis rate suggest that the acid-catalyzed cleavage of these compounds involves a rapid initial protonation of the benzimidazole ring and a subsequent rate-limiting heterolysis of the protonated substrate to form a free nitrogen base and an oxocarbenium ion derived from the ethoxyethyl group.The values obtained for the entropy of activation are consistent with the assumed u nimolecular nature of the rate-limiting step.The effects of 2-substituents on the acidities of the protonated substrates and their heterolysis rates have been compared.The latter partial reaction has been suggested to be the subject of steric acceleration.