7137-32-8Relevant articles and documents
METHOD FOR MANUFACTURING A 6-SUBSTITUTED 1-METHYL-1H-BENZIMIDAZOLE DERIVATIVE AND AN INTERMEDIATE OF SAID METHOD
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Page/Page column 11-12, (2012/09/25)
A method for manufacturing a 6-substituted 1-methyl-1H-benzimidazole derivative represented by the formula (IV) wherein R3 represents a hydrogen atom or a C1-C4 alkyl group. A 4-substituted N2-methylbenzene-1,2-
Synthesis and Thermolysis of Ketal Derivatives of 3-Hydroxy-1,2-dioxolanes
Baumstark, A. L.,Vasquez, P. C.,Chen, Y.-X.
, p. 6692 - 6696 (2007/10/02)
3--3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (2), 3-methoxy-3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (3), and 3-acetoxy-3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (4) were synthesized from the corresponding 3-hydroxy-1,2-dioxolane (1a) under basic conditions. 3-Acetoxy-4,4-dimethyl-3,5,5-triphenyl-1,2-dioxolane (5) was also synthesized via this approach.Under acidic conditions, 3-hydroxy-1,2-dioxolane 1a underwent quantitative decomposition to phenol and 3,3-dimethyl-2,4-pentanedione.This competing degradation was dependent on the nature of the substituents at position-5.Methyl groups at position-5 slowed the degradative rearrangement whereas phenyl groups favored it. 3-Methoxy- and 3-(allyloxy)-4,4,5,5-tetramethyl-3-phenyl-1,2-dioxolanes (6, 7) were synthesized under acidic conditions from the appropriate 1,2-dioxolane precursors and the corresponding alcohols.At 60 deg C, derivatized 1,2-dioxolanes 2-7 were found to be more stable than the corresponding 3-hydroxy-1,2-dioxolanes.The first order rate constants for the thermolysis of 1,2-dioxolanes 2-7 were determined.Product studies showed that thermolysis of 2-5 yielded pairs of ketones and derivatized carboxylic acids.In addition to R-group migration products, an acetoxy migration product was observed for the thermolysis of 4.Thermolysis of 6 at 60 deg C in benzene yielded methyl benzoate and pinacolone, quantitatively.Thermolysis of 7 yielded products analogous to those for 6.No evidence for internal trapping of radicals by the carbon-carbon double bond of the allyloxy group in 7 was found.The thermolysis appeared to proceed with peroxy bond homolysis as the rate-determining step.Subsequent β-scissions of the intermediate 1,5-oxygen diradical with interesting rearrangements that show a high preference for alkyl vs phenyl migration account for the observed product distributions.The results suggest that the β-scission/rearrangement mechanism may not be concerted but rather stepwise to yield 1,3-diradical and carbonyl fragments.
Reactions of Tris(dialkylamino)phosphines with Carbonyl Compounds
Hargis, J. H.,Mattson, G. A.
, p. 1597 - 1602 (2007/10/02)
The reactions of hexamethylphosphorous triamide and some cyclic analogues with anhydrides, acid chorides, and esters are reported.A mechanism is postulated which involves nucleophilic attack of trivalent phosphorus upon the carbonyl carbon, followed by phosphorane formation and a concerted fragmentation to products.