THE ACETOLYSES OF THE ALPHA AND BETA METHYL D-GLUCOPYRANOSIDE TETRAACETATES

1955 ◽  
Vol 33 (1) ◽  
pp. 148-162 ◽  
Author(s):  
R. U. Lemieux ◽  
W. P. Shyluk ◽  
G. Huber

The acetolyses of the alpha and beta methyl D-glucopyranoside tetraacetates in 1:1 acetic acid – acetic anhydride 0.5 M with respect to sulphuric acid were followed at 25 °C. by isotopic dilution analysis of products isolated after various intervals of time. The reaction of the α-glucoside was found to proceed mainly with inversion of the anomeric center. On the other hand, the β-glucoside was found to undergo acetolysis with retention of configuration concurrent with anomerization. It was shown that the polarimetric changes observed in the course of the reactions could be satisfactorily accounted for on the basis of these reaction routes. Reaction mechanisms are suggested.

1913 ◽  
Vol 32 ◽  
pp. 12-16
Author(s):  
Alexander Charles Cumming ◽  
E. W. Hamilton Smith

So many papers have appeared on this subject that some apology seems desirable before making an additional contribution. The amount of published work on reduction with sulphurous acid is in itself an indication that many workers have found difficulties. It has been shown that the reduction does not take place in presence of large excess of hydrochloric or sulphuric acid, but the reduction will still occur while the reaction of the solution is strongly acid. On the other hand, Hillebrand (“Analysis of Silicate and Carbonate Rocks,” U.S. Bulletin, 442, p. 113) states if the solution after addition of sulphite is red in colour, it is too alkaline and acid must be added.


2013 ◽  
Vol 9 ◽  
pp. 8-14 ◽  
Author(s):  
Yan Sun ◽  
Jing Sun ◽  
Chao-Guo Yan

A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.


1977 ◽  
Vol 32 (6) ◽  
pp. 701-704 ◽  
Author(s):  
Gert Kollenz ◽  
Erich Ziegler ◽  
Walter Ott ◽  
Gert Kriwetz

4-Benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dione (1) reacts with aldehydes or ketones via the acylketene-intermediate (2) yielding the 1,3-dioxin-4-ones (3). The aldehyde derivatives (3 a-e) can be converted into the anilino-chalcone (5) or the anilino acrylic acid (6) by treating with aniline at 20 °C. 6 and diazomethane combine to the acrylic acid methyl ester (7), which by heating (200 °C) is cyclisized to the quinolin-4-ole (8). On the other hand, the keto derivatives 3f-h and aniline give the dibenzoyl acetic acid anilide (9).


1966 ◽  
Vol 44 (17) ◽  
pp. 2009-2014 ◽  
Author(s):  
R. T. Coutts ◽  
J. B. Edwards

4-(2-Nitrobenzylidene)-2-pyrazolin-5-ones (I) were best prepared by heating o-nitrobenzaldehyde and 2-pyrazolin-5-ones in acetic anhydride containing fused sodium acetate (cf. Erlenmeyer azlactone synthesis). Pyrazolones of type I were reductively cyclized with cyclohexene and palladium–charcoal, and gave 3a,4,9,9a-tetrahydro-9-hydroxy-1H-pyrazolo-[3,4-b]quinolines (II) which, as expected, were amphoteric compounds. Of the three other methods of reduction used in this study, two (zinc and acetic acid; sodium borohydride and palladium–charcoal) were capable of producing pyrazoloquinolines, but were less reliable. The other method employed (hydrazine hydrate and palladium–charcoal) caused degradation of the pyrazolone molecule in the two cases examined, and in both, bis(2-aminobenzylidene) hydrazine (V) was the reduction product isolated.


2019 ◽  
Vol 7 (1) ◽  
Author(s):  
Sarka Msallamova ◽  
Milan Kouril ◽  
Kristyna Charlotte Strachotova ◽  
Jan Stoulil ◽  
Kateryna Popova ◽  
...  

Abstract Historical museums and depositories contain collections with a number of lead objects or historical documents with lead seals. Lead is a metal which has good corrosion resistance under atmospheric conditions. On the other hand, lead corrodes in an activity in an environment which contains volatile organic compounds (mainly acetic acid and formic acid). In a depository environment, sources of volatile compounds can be the historical documents themselves, wood, plastics (those made from cellulose acetate), polyvinyl acetate adhesives, varnishes, oil or emulsion paints, etc. The aim of this work was to compare the efficiency of commercial adsorbents (activated carbon, activated alumina, zeolite, and bentonite) in the acetic acid vapours. The lead corrosion rates were determined by using lead resistometric probes. Activated alumina and activated carbon were found to be the most effective adsorbents of acetic acid vapours. On the other hand, the available zeolite had the worst sorption ability compared with the other tested substances.


1977 ◽  
Vol 32 (4) ◽  
pp. 430-433 ◽  
Author(s):  
Mohamed Hilmy Elnagdi ◽  
Ezzat Mohamed Zayed ◽  
Ezzat Mohamed Kandeel ◽  
Sherif Mahmoud Fahmy

3-Amino-4-phenylhydrazono-2-pyrazolin-5-one (1) reacts with isothiocyanate to yield the corresponding pyrazolylthiourea derivatives (2 a-c). Whereas 2 a reacted with hydrazines to yield the pyrazolylamino-1,2,4-triazoles (3 a, b), it cyclised into the pyrazolo-[3,4-e]-as-triazine derivative (4) upon treatment with concentrated sulphuric acid. On the other hand, the pyrazolo[1,5-c]-S-triazine derivative (5) was formed from reaction of 2a with ethanolic sodium ethoxide.3-Amino-2-pyrazolin-5-one (8) reacted with ethyl acrylate to yield a mixture of the 4-dialkylated derivative (9) and the pyrazolo[3,4-b]pyrone (11). Compound 11 could be converted into the corresponding pyrazolo[3,4-b]pyrones (12) and (13) by the action of acetic acid hydrochloric acid mixture and of concentrated sulphuric acid, respectively.


1995 ◽  
Vol 48 (12) ◽  
pp. 1969 ◽  
Author(s):  
SD Barker ◽  
K Wilson ◽  
RK Norris

The nitration of α- and β- acylnaphthalenes with copper(II) nitrate in acetic anhydride or nitric acid/acetic acid mixtures gives high yields of the corresponding mononitro compounds. The assignment of constitution to these products is made on the basis of extensive 1H n.m.r. chemicl shift and coupling constant data. In the case of α- acylnaphthalenes, with the notable exception of α- pivalonaphthone, nitration occurs in the α-positions of the unsubstituted ring to give mixtures of 5- and 8-nitro compounds. α- Pivalonaphthone gives appreciable amounts of the 4-nitro compound and also of the 8-nitro compound. This result indicates that the pivaloyl group does not shield the 8-position sterically to any significant extent and is effectively electronically neutral, unlike the other acyl substituents , in allowing attack at the α-position (position 4) of the acylated ring. This result is ascribable to the lack of coplanarity of the pivaloyl group with the naphthalene system. All of the β- acylnaphthalenes gave mixtures of 4-, 5- and 8-nitro derivatives in proportions that did not vary significantly with the nature of the acyl group.


1976 ◽  
Vol 29 (4) ◽  
pp. 865 ◽  
Author(s):  
CP Joshua ◽  
PK Ramdas

Photolysis of 2,2'-dinitrodiphenylmethane (1) in isopropyl alcohol affords dibenzo[c,f][l,2]diazepin-11-one 5-oxide (7) as the major product. Dibenzo[c,f][l,2]diazepin-11-one 5,6-dioxide (6), acridone (8) and 2,2'-dinitrobenzophenone (9) are also formed in the reaction. Irradiation of (1) in ethanolic sulphuric acid on the other hand yields 3-(2'-nitropheny1)-2,l-benzisoxazole (11) as the major product; small amounts of (7), (8) and (9) are also isolated. Photoconversion of (1) in triethylamine and alcoholic triethylamine proceeds very slowly and compounds (7), (8) and (9) only are isolated from the photolysed solution. Some aspects of the mechanism are discussed.


Sign in / Sign up

Export Citation Format

Share Document