High-pressure reactions of 2-methylfuran with activated carbonyl compounds, n-butyl and (R)-menthyl glyoxylate are described. The reactions carried out in toluene under 11 kbar at 50-degrees-C afforded ca 1:1 mixtures of two regioisomeric products 4 and 5, which after benzylation were separated by column chromatography.

ChemInformVolume 21, Issue 6 Heterocyclic Compounds ChemInform Abstract: The Stereochemical Course of the High-Pressure Reaction of 2,5-Dialkylfurans with Diethyl Mesoxalate. J. JURCZAK, J. JURCZAK Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorS. BELNIAK, S. BELNIAK Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorM. CHMIELEWSKI, M. CHMIELEWSKI Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorT. KOZLUK, T. KOZLUK Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorS. PIKUL, S. PIKUL Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorG. JENNER, G. JENNER Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this author J. JURCZAK, J. JURCZAK Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorS. BELNIAK, S. BELNIAK Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorM. CHMIELEWSKI, M. CHMIELEWSKI Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorT. KOZLUK, T. KOZLUK Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorS. PIKUL, S. PIKUL Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this authorG. JENNER, G. JENNER Inst. Org. Chem., Polish Acad. Sci., 01-224 Warszawa, PolandSearch for more papers by this author First published: February 6, 1990 https://doi.org/10.1002/chin.199006147Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume21, Issue6February 6, 1990 RelatedInformation

The high-pressure reaction of 2,5-dimethylfuran with various activated carbonyl compounds: n-butyl, t-butyl, and (R)-menthyl glyoxylates, methyl pyruvate, and methyl and ethyl mesoxalates, gives the single products of general structure 3, corresponding to formal electrophilic substitution at the methyl group of the heteroaromatic system.

La forme cis-transoide du compose du titre cristallise dans le systeme triclinique avec le groupe d'espace P1. La forme cis-cisoide cristallise dans le systeme orthorhombique avec le groupe d'espace P2 1 2 1 2 1 . Affinement de la structure jusqu'a 0,051 et 0,66 respectivement

AbstractDie Umsetzungen von Furanen, Thiophenen, Pyrrolen sowie N‐Methyl‐pyrrolen mit und ohne Methylgruppen in 2‐ und/oder S‐Stellung mit Carbonylverbindungen (II) werden unter teils geringen, sowie sehr hohem Druck untersucht.

AbstractDie Hochdruckreaktion des Furans (I) mit den Chinonen (II) führt zu den endo‐Addukten (III), die in Lösung unter Retro‐Diels‐Alder‐Reaktion wieder die Ausgangsverbindungen liefern.

AbstractDie Hochdruck‐Diels‐Alder‐Reaktion von (I) und (II) führt zu dem Gemisch der Addukte (III) und (IV), während die analoge Reaktion von (V) und (II) je nach Eduktverhältnis nur Verbindung (VI) oder die Verbindungen (VI)‐(VIII) liefert.

KMnO4-hydroxylation of 6-methyl-2,7-dioxabicyclo[3.2.0]hept-3-ene (2) occurs from the exo side and leads—after reorganization of the hemiacetal systems—to 3-deoxy-dl-streptose (isolated as the 1,2-O-isopropylidene derivative 11). The structure of 11 was proved by conversion to 3,5-dideoxy-1,2-O-isopropylidene-3-C-methyl-β-dl-arabino-pentofuranose.

AbstractDie KMnO4‐Hydroxylierung des Dioxabicycloheptens (I) erfolgt von der exo‐Seite und führt ‐ nach Reorganisation des Halbacetalsystems ‐ zur Titelverbindung (II), die in Form der Isopropylidenderivate (III) und (IV) isoliert wird.

AbstractFuran (I) reagiert mit den Benzochinonen(II) zu den endo/exo‐ Addukten (III)+(IV) [bei Raumtemp. instabile Verbindungen; Aufnahme der 1H‐ NMR‐Spektren bei ‐50°C ].

AbstractDie Reaktion des Furans (I) mit dem Benzochinon (II) bei hohem Druck liefert Gemische der endo‐ (III) und exo‐ Isomeren (IV), wobei der Anteil des exo‐Isomeren (IV) mit zunehmendem Druck wächst; die Änderung der Reaktionstemp. hat demgegenüber praktisch keinen Ein‐ ?uss.

Hydroxylation of 6-substituted 2,7-dioxabicyclo[3.2.0]hept-3-enes (I, XIV and XV) with m-chloroperoxybenzoic acid occurs mainly from the exo side and leads to the corresponding 3-m-chlorobenzoates of trans-3,4-diols (VI, XVIII and XXII). Hydroxylation of substrates XIV and XV with potassium permanganate leads to 3-deoxy-3-C-formyl-DL-arabino-aldofuranoses. Epimerization at the formyl group-bearing carbon atom occurs during the reorganization of dihydroxylated dioxabicycloheptanes in basic medium.

AbstractUnter hohem Druck reagieren die Carbonylverbindungen (II) mit dem Dimethylfuran (I) zu den Addukten (III).

For the first time a successful [2 + 4]‐cycloaddition of furan (1) with simple 1,4‐benzoquinones 2 has been realized.

Abstract(Taprolactam (I) wird über die Stufe des Imidchlorids (II) mit Alkoholcn in (,Taprolactimethcr (III) übergeführt.

AbstractDie Hydroxylierung der Dioxabicycloheptene (I) mit der Persäure (II) in aprotischem Medium erfolgt hauptsächlich von der exo‐ Seite und führt zu den Estern (III).

AbstractDie Cycloaddition des Furans (I) an das Anhydrid (II) führt nur dann zum Produkt (III), wenn ein Druck von 22 kbar angewendet wird.

AbstractAs an active diene (more active than furan itself), 3,4‐dimethoxyfuran (1) affords with many dienophiles the respective cycloadducts in a high yield [2]. It has recently been found that under thermal conditions 1 easily reacts with maleic anhydride and its monomethyl derivative, but not with dimethylmaleic anhydride (2) [3]. This is probably due to steric hindrance resulting from the location of two methyl groups on the double bond of the dienophile. Since all Diels‐Alder reactions in particular those with steric hindrance are pressure‐sensitive [4]. we resolved to perform the title reaction under conditions of static high pressure.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of 3-substituted furansAleksander Zamojski and Tomasz KozlukCite this: J. Org. Chem. 1977, 42, 6, 1089–1090Publication Date (Print):March 1, 1977Publication History Published online1 May 2002Published inissue 1 March 1977https://pubs.acs.org/doi/10.1021/jo00426a038https://doi.org/10.1021/jo00426a038research-articleACS PublicationsRequest reuse permissionsArticle Views388Altmetric-Citations42LEARN 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 InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts