Tetramethylthiophene and Tetramethylfuran

Gaertner, Russell; Tonkyn, Richard G.

doi:10.1021/ja01156a515

Cited by 40 publications

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“…Analysis by vpc of Extract I from the 12-, 18-, and 25-h reactions revealed the presence of an additional product with longer retention time (13.8 min), which was found to be 4-hydroxy-2,4-dimethyl-2-pentenoic acid y-lactone (22).' These analyses were carried out on samples that had stood in air for several days.…”

Section: Dihydro-22-55-tetramethyl-3(2h)-furanone (1)mentioning

confidence: 99%

“…The mixture of adducts (22,23) was repeatedly crystallized from heptane to give the exo adduct as long needles, m 96. Equimolar solutions of maleic anhydride and tetramethylfuran in CHC13 were mixed and the 'H nmr spectrum of the resulting solution was recorded after approximately 1, 3, and 6 min.…”

Section: Maleic Anhydride Adducts Of Tetramethylfuran (25)mentioning

confidence: 99%

“…When the reaction mixture was heated for 6 h at 120"C, this new product was formed almost exclusively. It was identified as tetramethylfuran (25) by comparison of it and its exo adduct with maleic anhydride with authentic samples (22,23).…”

mentioning

confidence: 99%

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Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids

Yates¹,

Burke²

1987

Can. J. Chem.

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Can. J. Chem. 65, 1695Chem. 65, (1987. Reaction of tetrahydro-2,2,5,5-tetramethyl-3(2H)-furanone (1) with 96 or ca. 100% sulfuric acid or hot polyphosphoric acid followed by aqueous quenching gave the following products: 2-hydroxy-2,5-dimethyl-4-hexen-3-one (3), 2,4,4-trimethyl-2-cyclopenten-1-one (7), 3,5,5-trimethyl-2-cyclopenten-1-one (8), tetrahydro-3,4,5,5-tetramethylfuran-2,3-diol ( l l ) , 2,5-dihydro-3,5,5-trimethyl-2-methylenefuran (17) and its dimer 20, 2,5-dihydro-2,3,5,5-tetramethyl-2-furanol (IS), 4-hydroxy-2,4-dimethyl-2-pentenoic acid y-lactone (22), 2,3,5-trimethyl-2-cyclopenten-1-one (23), and tetramethylfuran (25). In 96% sulfuric acid the products arise by ring opening, ring opening followed by reclosure to carbocyclic products, methyl migration from C-2 to C-3 to give rearranged furan derivatives, and oxidation. Inca. 100% sulfuric acid or hot polyphosphoric acid further methyl migrations can occur to give 23 and 25.PETER YATES et PATRICK MICHAEL BURKE. Can. J. Chem. 65, 1695Chem. 65, (1987.La reaction de la tetrahydro tCtramCthyl-2,2,5,5 2H-furannone-3 (1) avec de I'acide sufurique a 96 ou t i environ 100% ou avec de l'acide polyphosphorique chaud, suivie par un piCgeage avec de l'eau, conduit aux produits suivants : l'hydroxy-2 dimethyl-2,5 hexkne-4 one-3 (3), la trimithyl-2,4,4 cyclopentkne-2 one-1 (7), la trimethyl-3,5,5 cyclopentkne-2 one-1 (8), le tetrahydro tCtramCthy1-3,4,5,5 furannediol-2,3 (11), le dihydro-2,5 trimethyl-3,5,5 mCthyl6ne-2 furanne (17) There have been many investigations of the reactions of organic compounds with strong acids (3, 4). Several of these have concerned substrates with saturated or unsaturated carbony1 functions. Less attention has been paid to carbonyl compounds containing other functional groups. We report on an investigation of the variety of reactions undergone by the keto ether 1 in strongly acidic media.3 We describe here the isolation and determination of the structures of the products formed in such reactions and plan, in a subsequent publication, to discuss the formation of these products in terms of the site(s) of protonation of 1 and the nature of the cationic intermediates.Compound 1 is readily available from the ynediol 2 (6). Reactions in strongly acidic media followed by aqueous quenching gave mixtures of products whose composition was dependent on both the nature of the medium and the time of reaction. These products were isolated by standard procedures and identified by their spectra (Tables 1 and 2) and by comparison in most cases with independently synthesized samples.Vapor phase chromatographic (vpc) analyses of product mixtures from 96% sulfuric acid showed that one compound was formed rapidly and that the amount of this product reached a maximum after 2 h and then fell to zero after several days. This compound was shown to be 3 by comparison with an authentic

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Section: Dihydro-22-55-tetramethyl-3(2h)-furanone (1)mentioning

confidence: 99%

Section: Maleic Anhydride Adducts Of Tetramethylfuran (25)mentioning

confidence: 99%

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Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids

Yates¹,

Burke²

1987

Can. J. Chem.

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“…1,4‐Dicarbonyl compounds are important intermediates in the synthesis of many bioactive heterocyclic scaffolds (Figure ) such as pyrrole derivatives, furans and thiophenes …”

Section: Introductionmentioning

confidence: 99%

Intermolecular Stetter Reactions on Morita‐Baylis‐Hillman Adducts: an Approach to Highly Functionalized 1,4‐Dicarbonyl Compounds

et al. 2017

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We reported herein an N‐heterocyclic carbene (NHC)‐mediated intermolecular Stetter reaction between oxidized Morita‐Baylis‐Hillman (MBH) adducts and a variety of aldehydes. This protocol allows the synthesis of highly functionalized 1,4‐dicarbonyl compounds. The reaction is an alternative approach to these compounds using commercially available starting materials. This metal‐free process exhibits a wide substrate scope, excellent atom economy, compatibility with functionalized substrates and mild reaction conditions. The 1,4‐dicarbonyl compounds were prepared in two steps via MBH reactions with overall yields up to 99 %. This protocol is easily scalable. The synthetic usefulness of this method was demonstrated in a high yield synthesis of a tri‐substituted pyrrole used as an advanced intermediate in the total synthesis of kinase inhibitors as well as in the synthesis of another heterocycles.

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“…To the best of our knowledge, in contrast to furan 1-7 and other dienes [8][9][10][11][12] , very little has been reported on the [4+2]-cycloaddition of quinones and other cycloenones to thiophenes in general and 2-aminothiophenes in particular. Direct addition of dienophiles in general [13][14][15] and quinonoid dienophiles in particular across the butadiene fragment of the thiophene ring system in a [4+2]-mode seems to be rare. Three cases of cycloaddition of 1,4-naphthoquinone to [c]anellated 2-aminothiophenes have been reported recently by Al-Saleh et al 16 .…”

Section: Introductionmentioning

confidence: 99%

Reactions of some annelated 2-aminothiophenes with two naphthoquinones

Fondjo¹,

Döpp²

2006

Arkivoc

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2- 5,6,thiophene-3-carbonitrile(1) and three 3-aminobenzopyrano [3,4-c]thiophenes (2a-c) were reacted with 2,3-dichloro-1,4-naphthoquinone (3a) and the parent 1,4-naphthoquinone (3b) in solution at reflux temperature. While from 1 only products of addition/dehydrogenation and chlorine substitution, respectively, were obtained, Diels-Alder addition of 2a-c to 3b followed by hydrogen sulfide elimination led to the polycycles 10a-c.

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Tetramethylthiophene and Tetramethylfuran

Cited by 40 publications

References 0 publications

Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids

Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids

Intermolecular Stetter Reactions on Morita‐Baylis‐Hillman Adducts: an Approach to Highly Functionalized 1,4‐Dicarbonyl Compounds

Reactions of some annelated 2-aminothiophenes with two naphthoquinones

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