Anhydride Adduct Research Articles

Diels-Alder Reaction. V. The Reaction of 2, 5-Dialkylhydroquinones and Maleic Anhydride.

The reaction of 2, 5-dialkylhydroquinones, 2-methyl-5-ethylhydroquinone (II), 2, 5-diethyl-hydroquinone (III), 2-methyl-5-propylhydroquinone (IV), and 2, 5-dipropylhydroquinone (V), with maleic anhydride was investigated. Of these hydroquinone homologs, (II) and (III) gave the maleic anhydride adducts, (VIIa) or (VIIb) and (VIII), respectively. The effect of alkyl groups on the reactivity of the hydroquinone homologs is discussed.

Infrared studies on the isomers of kamlolenic acid

SummaryThecis‐trans and positional configuration of α‐and β‐kamlolenic acids have been investigated. Infrared data of the two isomers, their acetyl derivatives and maleic anhydride adducts, and the permanganate oxidation products of the addition compounds, together with the selective epoxidation of the exocyclic double bond of the maleinated derivatives, have been used to confirm the structure of the three conjugated double bonds in α‐kamlolenic acid ascis‐9‐trans 11‐trans 13. and β‐kamlolenic acid astrans 9‐trans 11‐trans 13.

Composition of Gum Turpentine of Pines. XXIV A Report on Two Asiatic Pines: Pinus armandi and P. bungeana

Composition of the total oil of P.armandi, both light (82% of the total) and heavy (18%) is approximately as follows: /- and dl-a-piaeae, 44%; /-camphene, 2%; /-/3-pinene, 4%; /-limonene, 17-18%; n-undecane, 1%; /-bornyl acetate, 6.5%; a bicyclic sesquiterpene, bi2, 116-118°, 3.5%; a bicyclic sesquiterpene related to cadalene, 9%; “albicaulol,” 1.5%; cembrene, 4.5%; a diterpene which gave a maleic anhydride adduct, 1%; pot residue and loss, 6%.P.bungeana turpentine is of a very simple composition: 60-65% d- and <//-a-pinene; 30-35% /-/3-pinene and about 2 or 3% of unidentified higher-boiling fractions, presumably sesquiterpenes.Composition of turpentine of P.bungeana, thus, differs very much from that of P.armandi. It also differs from P.gerardiana in almost complete absence of sesquiterpenes, and in its /3-pinene being levorotatory.

The Diels-Alder Reaction and the Rearrangement of the Maleic Anhydride Adducts of 6,6-Dimethylfulvene

The Diels-Alder Reaction and the Rearrangement of the Maleic Anhydride Adducts of 6,6-Dimethylfulvene

The infrared spectra and the structural relationships between alpha‐ and beta‐eleostearic acids and their maleic anhydride adducts

SummaryThe cis, trans, and positional configuration of alpha‐and beta‐eleostearic acids have been investigated. The maleic anhydride adducts of alpha‐and beta‐eleostearic acids were prepared and subjected to hydrogenation, selective epoxidation, and esterification. Two epoxy derivatives of the maleinated beta‐eleostearic acid were isolated and characterized. Infrared spectra of these maleic anhydride adducts and their various derivatives have been measured in the rock salt region, 2–12 microns. These infrared data together with chemical evidence have been used to confirm the structure of alpha‐eleostearic acid as 9‐cis, 11‐trans, 13‐trans octadecatrienoic acid and beta‐eleostearic acid as 9‐trans, 11‐trans, 13‐trans octadecatrienoic acid.Complete infrared spectra are presented for authentic samples of alpha‐and beta‐tung oil, China wood oil, oiticica oil, and alpha‐and beta‐eleostearic acids. Infrared absorption curves are presented, including the maleic anhydride adducts of alpha‐and beta‐eleostearic acids, various derivatives of these adducts and the following reference compouds: maleic anhydride, dimethyl maleate, dimethyl fumarate, the butadiene‐maleic anhydride adduct and its dimethyl ester.

Alternative methods for dehydrating castor oil

SummaryCastor oil can be effectively dehydrated by non‐conjugated oil‐maleic anhydride adducts to give use‐ful paint or yarnish oils. Castor acids dehydrated in the presence of alumina form diene acids of 60% two double bond conjugation. The glyceride from these acids dries more rapidly to a tack‐free film than conventional dehydrated castor oil. In both of these processes the course of dehydration is believed to be the decomposition of esters of the alcohol groups in ricinoleic acid. Acidic ion exchange resins exert some catalytic effect in the dehydration of castor oil, but the oil so made is inferior in color and film properties.

The Maleic Anhydride Adducts of Sorbic Acid and Methyl Sorbate

The Maleic Anhydride Adducts of Sorbic Acid and Methyl Sorbate

The Maleic Anhydride Adduct of N-Phenyl-3,5-diethyl-2-propyl-1,4-dihydropyridine

The Maleic Anhydride Adduct of N-Phenyl-3,5-diethyl-2-propyl-1,4-dihydropyridine

A Pyrolysis Product of the Sorbic Acid—Maleic Anhydride Adduct

A Pyrolysis Product of the Sorbic Acid—Maleic Anhydride Adduct

Synthesis of a benzene ring with a ten-membered para-bridge.

WE have recently investigated the synthesis of para-bridged benzene rings by dehydrogenation of maleic anhydride adducts of large ring dienes1. As this method is very laborious, we decided to find the lowest possible number of carbon atoms necessary to form a para-bridge starting from a preformed benzene ring, and then to use our dehydrogenation method systematically only for smaller bridges, which cannot be synthesized by ring closure. We have used the acyloin ring closure as described by Prelog and collaborators2, and cyclized the diester prepared according to Ruzicka and collaborators3 from pure p-xylene. Surprisingly, we obtained the acyloin in 70 per cent yield (b.p. 150–160°, 0.3 mm. mercury). After standing in the icebox, it solidified to a very low-melting crystalline solid (found: C, 78.07; H, 8.93; calculated for C16H22O2; C, 78.01; H, 9.00 per cent). In alcohol with platinum oxide, this compound took up one mole of hydrogen and the corresponding diol was obtained (m.p. 102–103°; found: C, 77.39; H, 9.73 per cent; calculated for C16H24O2: C, 77.37; H, 9.74 per cent). The diol consumed the theoretical amount of periodic acid. The high yield of the pure acyloin is interesting, as under identical conditions the cyclization reaction gives a yield of only 58 per cent cyclotetradecoin. It seems that the shortest para-bridge will have less than ten and more than six carbons, which is the length of the shortest bridge in the meta-position4.

THE OZONIZATION OF THE MALEIC ANHYDRIDE ADDUCT OF DEHYDROERGOSTERYL ACETATE

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTHE OZONIZATION OF THE MALEIC ANHYDRIDE ADDUCT OF DEHYDROERGOSTERYL ACETATERobert H. Levin, Mildred M. Wesner, and Elizabeth M. MeinzerCite this: J. Am. Chem. Soc. 1948, 70, 8, 2834–2835Publication Date (Print):August 1, 1948Publication History Published online1 May 2002Published inissue 1 August 1948https://doi.org/10.1021/ja01188a532RIGHTS & PERMISSIONSArticle Views24Altmetric-Citations2LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (238 KB) Get e-Alerts Get e-Alerts

Autoxidation of fats. I. Preparation and oxidation of alkylbenzene‐maleic anhydride adducts

SummaryIt has been shown that certain alkylbenzenes having a hydrogen atom on the alpha carbon atom react with maleic anhydride to form compounds analogous to the hydroperoxides produced by autoxidation of the alkylbenzenes. The structure of these products has been determined by oxidation with aqueous permanganate and the results have been applied, together with other data, to demonstrate that the reaction proceeds by a free radical chain mechanism involving the abstraction of a hydrogen atom from the alpha carbon atom. In view of the analogy between the products obtained in this investigation and in autoxidation, it is suggested that autoxidation is propagated in a similar manner.

Reaction of β-Naphthol with l-α- and l-β-Phellandrene

SOME years ago, Goodway and West1 reported that low yields of the maleic anhydride adduct corresponding to α-phellandrene were obtainable from β-phellandrene, and it was considered probable that the l-α-phellandrene adduct isolated was derived by the thermal decomposition of the primary resinous material obtained from the l-β-phellandrene.

32. Application of the diene synthesis to terpenoid compounds. Part II. Observations on the esters derived from some maleic anhydride adducts

32. Application of the diene synthesis to terpenoid compounds. Part II. Observations on the esters derived from some maleic anhydride adducts