Acrylic acid nitro

Types of compounds are arranged according to the following system hydrocarbons and basic heterocycles hydroxy compounds and their ethers mercapto compounds, sulfides, disulfides, sulfoxides and sulfones, sulfenic, sulfinic and sulfonic acids and their derivatives amines, hydroxylamines, hydrazines, hydrazo and azo compounds carbonyl compounds and their functional derivatives carboxylic acids and their functional derivatives and organometallics. In each chapter, halogen, nitroso, nitro, diazo and azido compounds follow the parent compounds as their substitution derivatives. More detail is indicated in the table of contents. In polyfunctional derivatives reduction of a particular function is mentioned in the place of the highest functionality. Reduction of acrylic acid, for example, is described in the chapter on acids rather than functionalized ethylene, and reduction of ethyl acetoacetate is discussed in the chapter on esters rather than in the chapter on ketones. 

OB —64.4% om solid, mp (blackens at 170D). Prepd by treating with lead acetate the 5-Nitro-furyl-j8-acrylic Acid (Ref 2). It is an expl comparable in sensitivity to TNT, but much less powerful (<50% TNT, by ballistic mortar test). Its thermal stability is satisfactory and it. is only moderately hygroscopic Refs 1) Beil, not found 2) R. McGill,... 

Acetylenes, 4-substituted-, 58, 3 Acrylic acid, ethyl ester, 56, 65 ACRYLIC ACID, 3-NITRO-, ETHYL... 

Nitro-phenyl)-acrylic acid ethyl ester... 

Nitropropanoic acid esters can be converted into acrylic acid derivatives by treatment with a slight excess of DBU in THF or DMSO at room temperature. If 3-nitro-propanoates are treated with two equivalents of LDA at -78 °C in THF/DMPU or THF/HMPA, however, the resulting dianion can be cleanly C-alkylated, and the product isolated without elimination of the nitro group [160, 161] (Scheme 5.57). Without the addition of a cosolvent (DMPU, HMPA, or quinuclidine N-oxide [161]) alkylation of the 3-nitropropanoate dianion does not proceed sufficiently quickly [160,161],... 

With excess nitrosyl chloride, a chloronitro product is obtained in certain cases, a wide variety of ste-roid-5-enes giving 5a-chloro-63-nitro derivatives in good yield (CH2CI2/CCI4, to 0 C, 2-24 h). Nitryl chloride adds to terminal alkenes (56-80%) and to acrylic acid derivatives (refs. 239,240 and references cited therein) at temperatures close to ambient. The reaction appears to be a radical one, the NO2 entering the terminal position whatever the electronic requirement of the alkene. 

SYNS AF-2 (presen-ative) FF FURYT-AMIDE FURYLFURAMIDE a-2-FURYL-5-NITRO-2-FURAN-ACYRLAMIDE 2-(2-FURYL)-3-(5-NITRO-2-FURYL)-ACRYLIC ACID AMIDE a-(FURYL)-P-(5-NITRO-2-FURYL)ACRYLIC AMIDE TOFURON... 

FURYL)-3-(5-NITRO-2-FURYL)ACRYLIC ACID AMIDE see FQNOOO... 

Nitrile, azo, and nitroso groups, and even the oxygen molecule, take part in such reactions, and acetylenic triple bonds in particular confer reactivity as philodiene. As for dienes, so for philodienes the reactivity depends on the constitution. Activating groups particularly favor addition. The most reactive components include <%,/ -unsaturated carbonyl compounds such as acrolein, acrylic acid, maleic acid and its anhydride, acetylenedicarboxylic acid, p-benzo-quinone and cinnamaldehyde, as well as saturated nitriles and <%,/ -unsaturated nitro compounds. Tetracyanoethylene also reacts with dienes.41,42 Conjugation of the double bond to an active group is not absolutely essential for a philodiene, for dienes add under certain conditions also to philodienes with isolated double bonds examples of the latter type are vinyl esters and vinyl-acetic acid. Ketenes do not undergo the Diels-Alder reaction with dienes, but instead yield cyclobutanone derivatives 43,44... 

Glucose esters of 3-N. (endecaphyllins) are responsible for the toxicity of Indigofera endecaphylla for grazing animals. 3-N. functions as suicide substrate of succinate dehydrogenase where the formed 3-nitro-acrylic acid adds to the active thiol group of the enzyme. The compound is formed biosynthetically in Penicillium atrovenetum from L-aspartic acid which is oxidized to the a-nitrosuccinate and then decarboxy-lated to furnish the aci-nitro form of 3-N.. Malonate and N-hydroxymalonamate appear to be intermediates in Indigofera spicata. 

Nitro-2-furfural phenylhydrazone added to a soln. of acrylic acid in benzene-tetrahydrofuran, then a soln. of Pb-tetraacetate in benzene added with stirring at room temp. 3-(5-nitro-2-furyl)-l-phenylpyrazole. Y 90%. F. e. s. T. Sasaki and T. Yoshioka, Bull. Chem. Soc. Japan 43, 1254 (1970). 

K-azodicarboxylate added during 15 min. to a soln. of 3-(5-nitro-2-furyl)acrylic acid in 1,2-dimethoxyethane-methanol, then glacial acetic acid in the same solvent mixture added dropwise during 5 hrs. followed by more glacial acetic acid during an additional 5 hrs., and stirred 12 hrs. -> 3-(5-nitro-2-furyl)propionic acid. Y 89%. P. B. Hulbert, E. Bueding and C. H. Robinson, J. Med. Chem. 16, 72 (1973). 

The antischistosome activity of nitrofuran compounds was further investigated. Comparison of 3-(5-nitro-2-furyl)-substituted derivatives of propionic, acrylic and propiolic acids showed that a vinyl group is necessary for activity.1 5 in derivatives of 3-(5-nitro-2-furyl) acrylic acid, the 5-nitro group was required for activity.12 In a group of (5-nitro-2-furyl)-vinyl heterocycles containing a weakly basic N in a specific position, both the vinyl group and the N were essential for antischistosome activity.1 ... 

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