Ketene Acetals. XXX. Alkylation of Dimethylketene Dimethylacetal

McElvain, S. M.; Aldridge, Clyde L.

doi:10.1021/ja01112a033

Cited by 28 publications

(5 citation statements)

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“…Reaction of 2,2-dimethylhexanoic acid (500 mg) according to general procedure method A afforded 83 mg (17%) of product 1r , isolated as colorless needles (recrystallized from ethanol): mp 92.5–92.9 °C (lit . mp 93–93.5 °C); 1 H NMR (500 MHz, DMSO- d 6 ) δ 6.97 (br s, 1H), 6.69 (br s, 1H), 1.42–1.37 (m, 2H), 1.28–1.19 (m, 2H), 1.18–1.09 (m, 2H), 1.03 (s, 6H), 0.86 (t, J = 7.3 Hz, 3H).…”

Section: Methodsmentioning

confidence: 99%

Hypervalent Iodine Catalyzed Hofmann Rearrangement of Carboxamides Using Oxone as Terminal Oxidant

et al. 2012

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Hofmann rearrangement of carboxamides to carbamates using Oxone as an oxidant can be efficiently catalyzed by iodobenzene. This reaction involves hypervalent iodine species generated in situ from catalytic amount of PhI and Oxone in the presence of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) in aqueous methanol solutions. Under these conditions, Hofmann rearrangement of various carboxamides affords corresponding carbamates in high yields.

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Section: Methodsmentioning

confidence: 99%

Hypervalent Iodine Catalyzed Hofmann Rearrangement of Carboxamides Using Oxone as Terminal Oxidant

et al. 2012

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“…In these cases the reaction period varies from a few days (methyl orthopropionate) to six weeks (ethyl orthobenzoate), but the reaction time has been cut to a few hours and the yields materially increased by carrying out the reaction in boiling ether (219) or petroleum ether (214). Such conditions ensure reaction temperatures below those at which decomposition of the imidate salt into the amide would predominate over formation of ortho ester.…”

Section: Preparation Of Ortho Esters By Alcoholysis Of Imidatesmentioning

confidence: 99%

The Chemistry of Imidates.

Roger¹,

Neilson²

1961

Chem. Rev.

393

160

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“…106 -1098, was synthesized by elimination of MeOH from trimethyl orthoisobutyrate [12]. Ketene Diethyl Acetal (19).…”

Section: Methodsmentioning

confidence: 99%

1,2‐Bis(trifluoromethyl)ethene‐1,2‐dicarbonitrile: Enol Ethers and Ketene Acetals as Cycloaddition Partners

Huisgen¹,

Desmaison²

2012

Helvetica Chimica Acta

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(E)‐ and (Z)‐1,2‐bis(trifluoromethyl)ethene‐1,2‐dicarbonitrile ((E)‐ and (Z)‐BTE, resp., =(E)‐ and (Z)‐2,3‐bis(trifluoromethyl)but‐2‐enedinitrile) were used as a stereochemical probe in studying (2+2) cycloadditions of acceptor with donor alkenes. The additions to methyl (E)‐ and (Z)‐propenyl ether gave rise to the eight conceivable cyclobutanes 8, although in different ratios in reactions of (E)‐ and (Z)‐BTE. The 19F‐NMR data served the structural assignment and the quantitative analysis. The mechanistic discussion is based on rotations and ring closures of the assumed 1,4‐zwitterionic intermediates. Dimethylketene dimethyl acetal, methylketene dimethyl acetal, and ketene diethyl acetal show an increasing rate in their reactions with BTE as well as in the equilibration of the cycloadducts.

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Ketene Acetals. XXX. Alkylation of Dimethylketene Dimethylacetal

Cited by 28 publications

References 0 publications

Hypervalent Iodine Catalyzed Hofmann Rearrangement of Carboxamides Using Oxone as Terminal Oxidant

Hypervalent Iodine Catalyzed Hofmann Rearrangement of Carboxamides Using Oxone as Terminal Oxidant

The Chemistry of Imidates.

1,2‐Bis(trifluoromethyl)ethene‐1,2‐dicarbonitrile: Enol Ethers and Ketene Acetals as Cycloaddition Partners

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