Free Radical Addition of Cyclic Ethers to Maleic Anhydride

Jacobs, Richard L.; Ecke, George G.

doi:10.1021/jo01046a025

Cited by 43 publications

(6 citation statements)

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“…Thus, the lower yield appears to arise from the radical reaction itself on TentaGel resin. As hydrogen atom abstraction from ethers is well precedented, it is possible that this is due to interference from the poly(ethylene glycol) linker. Depending on the age of the resin and exposure to oxygen and light, TentaGel resins are also susceptible to peroxide formation, which is likely to be detrimental to these reactions.…”

Section: Resultsmentioning

confidence: 99%

Intermolecular Conjugate Addition of Alkyl Radicals on Solid Phase

and

Ganesan

1999

J. Comb. Chem.

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The conjugate addition of alkyl radicals, generated photolytically from the corresponding Barton esters, to acrylate immobilized on solid-phase was investigated. Using cross-linked polystyrene, acrylic acid was loaded with either the Wang or Rink linkers, and the reactions were carried out with 10 equiv of Barton ester. The yields following resin cleavage by trifluoroacetic acid were comparable to Barton's solution-phase results. TentaGel resins gave approximately 15% poorer yields, possibly due to radical quenching by the poly(ethylene glycol) spacer. With the Barton ester from cyclopent-2-enylacetic acid, the initial product of conjugate addition is capable of further intramolecular cyclization followed by attack of a second acrylate chain, resulting in polymer cross-linking.

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Section: Resultsmentioning

confidence: 99%

Intermolecular Conjugate Addition of Alkyl Radicals on Solid Phase

and

Ganesan

1999

J. Comb. Chem.

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“…Conventional radical initiators such as triethylborane and dibenzoyl peroxide were totally inefficient. When triethylborane was used, ethyl adduct 2b was produced with no detectable amount of 3a in the crude product.…”

Section: Initiation Stepmentioning

confidence: 99%

Exploration of Dimethylzinc‐Mediated Radical Reactions

Yamada

Tomioka

2015

The Chemical Record

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“…Found: C, 51.89; H, 5.49. Tetrahydro-2-furylmaleic Acid (10).-/The dimethyl tetrahydro-2-furylmaleate (4) was saponified as above and diacid 10 was obtained as colorless crystals (crystallized from chloroform-30-600 petroleum ether): mp 84-86°; ir (CHCh) 3600-2500 br, 1700, 1645, and 1065 cm-1; nmr (CDCh) S 1.8-2.2 (m, 4 H), 3.7-4.2 (m, 2 H), 5.4-5.8 (m, 1 H), 6.65 (d, 1 H, J = 1.5 Hz, vinylic proton), and 9.3 br (s, 2 H, absent when washed with D20). The 70-eV mass spectrum of 10 was very similar to that of its isomer 5 and demonstrated its base peak at m/e 168 (M+ -H20).…”

Section: Singhmentioning

confidence: 99%

“…Tetrahydro-2-furylsuccinic Anhydride (9).-The title compound 9 was obtained as a colorless, mobile liquid in 50% yield by peroxide-initiated free-radical addition of maleic anhydride to tetrahydrofuran according to the method of Jacobs and Ecke. 10 The adduct 9, bp 107-111°( 0.1 mm), had the following spectral data: ir (neat) 1865, 1792, 1225, 1070, and 925 cm""1; nmr (CDC13) 1.8-2.4 (m, 4 H, methylenes of the furyl ring), 2.8-3.5 (m, 3 H, anhydride ring protons), 2.6-4.0 (m, 2 H, -CH2O-), and 4.1-4.5 (m, 1 H, -CH2OCH-).…”

Section: Singhmentioning

confidence: 99%