[2+4]-Cycloaddition of fluoroolefins and fluoroazomethines with furan

Al'bekov, V. A.; Benda, Aleš; Gontar, A. F.; Sokol'skii, G. A.; Knunyants, I. L.

doi:10.1007/bf01455502

Cited by 6 publications

(3 citation statements)

References 2 publications

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“…Dry flash column chromatography gave (with ether-light petroleum) the aziridine 5 (0.28 g, 39%) mp 83. 7 An examination of the 1 H NMR spectrum of the oil before chromatographic purification showed that it was identical to that of the aziridine 5. A solution of 2-azidoacrylic acid benzyl ester 16 (0.97 g, 4.78 mmol) in dry toluene (100 ml) was heated at 110 ЊC for 3-5 h, until all the starting material had decomposed (TLC).…”

Section: Methyl 3-(26-dichlorophenyl)-2-(25-dimethyl-5-hydroxy-25-dih...mentioning

confidence: 98%

Diels–Alder reactions of alkyl 2H-azirine-3-carboxylates with furans

Alves

Azóia

Bickley

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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Methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate 1 and furan give the aziridine 2 by a Diels-Alder cycloaddition reaction. The hydrolysis of compound 2 leads to a dihydrofuranol 11 by cleavage of a C-N bond. X-Ray crystal structures of compounds 2 and 11 have been determined. Compound 2 reacts with alcohols in a similar way to give 2-alkoxy-2,5-dihydrofurans as mixtures of cis and trans isomers. The structures of these compounds have been determined from an X-ray crystal structure of one of the methyl ethers, the trans isomer 13. The reaction of the azirine 1 with 1,3-diphenylisobenzofuran leads to the formation of two isomeric 1 : 1 adducts that have been identified as the products of endo and exo cycloaddition, 3 and 4. The endo isomer 3 is converted into the exo isomer 4 by heat. Similar Diels-Alder reactions have been carried out between furans and benzyl 2H-azirine-3-carboxylate 6. Hydrolysis of the adduct 7 formed with furan again produces a dihydrofuranol 25 as the major product together with three minor products, two of which are 1-azabicyclo[4.1.0]hept-3-ene-2,5-diols 27 and 28 that result from CO bond cleavage. Protection of the mixture of alcohols with TBS triflate gives the bis(TBS) ether 31 of the trans-1-azabicyclo[4.1.0]hept-3-ene-2,5-diol as the major product, showing that this ring system can be produced from the dihydrofuranol 25. The bis(TBS) ether 30 of the cis-2,5-diol is a minor product and its structure has been established by independent synthesis through a Diels-Alder reaction between the azirine 6 and 1,4-bis(tert-butyldimethylsilyloxy)butadiene 32.

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Section: Methyl 3-(26-dichlorophenyl)-2-(25-dimethyl-5-hydroxy-25-dih...mentioning

confidence: 98%

Diels–Alder reactions of alkyl 2H-azirine-3-carboxylates with furans

Alves

Azóia

Bickley

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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“…Finally, [4 + 2] cycloaddition of perfluoropropen-1-yl sulfonyl fluoride with furane led to the formation of Diels-Alder adduct 17 in good yield. [147] Alkynyl sulfonyl fluorides were also introduced into [3 + 2] cycloadditions with nitrile oxides, nitrones, azides, diazoalkanes, azomethine ylides, sulfonium ylides, sydnones, hydrazonoyl chlorides, as well as [4 + 2] and formal [5 + 2] cycloadditions (Scheme 17). [148] In addition to that, their multistep heterocyclizations providing oxazole [37,[149][150][151] and oxadiazole [36] derivatives were also reported.…”

Section: Methodsmentioning

confidence: 99%

“…Reaction of α‐bromovinyl sulfonyl fluoride 15 with halogenoximes or aliphatic azides under basic conditions gave isoxazoles 16 [124,145] and N ‐substituted triazoles, [145,146] respectively. Finally, [4+2] cycloaddition of perfluoropropen‐1‐yl sulfonyl fluoride with furane led to the formation of Diels‐Alder adduct 17 in good yield [147] …”

Section: Chemoselective Reactions Of Functionalized Sulfonyl Fluoridesmentioning

confidence: 99%

Chemoselective Reactions of Functionalized Sulfonyl Halides

Liashuk,

Andriashvili,

Tolmachev

et al. 2023

The Chemical Record

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Chemoselective transformations of functionalized sulfonyl fluorides and chlorides are surveyed comprehensively. It is shown that sulfonyl fluorides provide an excellent selectivity control in their reactions. Thus, numerous conditions are tolerated by the SO2F group – from amide and ester formation to directed ortho‐lithiation and transition‐metal‐catalyzed cross‐couplings. Meanwhile, sulfur (VI) fluoride exchange (SuFEx) is also compatible with numerous functional groups, thus confirming its title of “another click reaction”. On the contrary, with a few exceptions, most transformations of functionalized sulfonyl chlorides typically occur at the SO2Cl moiety.

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1,1,2,3,3,3-Hexafluoropropene

Walkowiak

Koroniak

2009

Encyclopedia of Reagents for Organic Synthesis

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[2+4]-Cycloaddition of fluoroolefins and fluoroazomethines with furan

Cited by 6 publications

References 2 publications

Diels–Alder reactions of alkyl 2H-azirine-3-carboxylates with furans

Diels–Alder reactions of alkyl 2H-azirine-3-carboxylates with furans

Chemoselective Reactions of Functionalized Sulfonyl Halides

1,1,2,3,3,3-Hexafluoropropene

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