Diels-Alder Reactions of trans-4,4,4-Trifluorocrotonic Acid. II

McBee, E. T.; Roberts, Carleton W.; Hsu, C. G.

doi:10.1021/ja01595a035

Cited by 8 publications

(4 citation statements)

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“…An interesting case is the trifluoromethyl substituent. In the reactions of trifluorocrotonic acid with acyclic dienes, such as isoprene, it is the carboxyl which apparently determines the structural orientation (206), probably owing to its greater conjugative ability to stabilize the transition state. With cyclopentadiene, however, the adduct with endo trifluoromethyl predominates 2:1 over that with endo carboxyl.…”

Section: (B) Dienophilesmentioning

confidence: 99%

“…1-Phenyl-1,3-butadiene and 4,4,4-trifluorocrotonic acid afford a 1:1 ratio of stereoisomeric adducts (206). The reaction of fumaryl chloride with several 2-substituted 1-phenyl-1,3-butadienes has been shown (20) to give adducts of configuration XLVII (R = CgHe; R" = H; R' = CH3, C2Hb, and COOCH3), but its addition to 1,2-diphenyl-1,3-butadiene appears to yield the other possible configuration.…”

Section: (B) Dienophilesmentioning

confidence: 99%

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Stereochemistry of the Diels-Alder Reaction.

Martin¹,

Hill²

1961

Chem. Rev.

317

110

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Section: (B) Dienophilesmentioning

confidence: 99%

Section: (B) Dienophilesmentioning

confidence: 99%

Stereochemistry of the Diels-Alder Reaction.

Martin¹,

Hill²

1961

Chem. Rev.

317

110

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“…At this stage, we found it convenient to separate the trans,endo-ester (4) from its trans,exo-isomer (7) by stereoselective enzymatic hydrolysis of the exo-ester by pig liver esterase (PLE), the endo-ester being unaffected. Our initial approach to racemic cis-6-trifluoromethylshikimic acid (14) was conducted with an ethyl ester group and we ran the synthesis up to ( +)-ethyl cis-6-trifluoromethylshikimate. This then failed to be saponified cleanly.…”

Section: Resultsmentioning

confidence: 99%

Stereospecific synthesis of racemic cis- and trans-6-trifluoromethylshikimic acids

Leroy¹,

Fischer²,

Wakselman³

1990

J. Chem. Soc., Perkin Trans. 1

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“…The Chemical Reactions Involved in the Experiment P-methoxyphenylacetylene(III) can be prepared according to a number of schemes reported in the literature (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), We first prepared 111 via the following route in which NaNH2 was used as the base in hexamethylphosphoramide as shown below.…”

mentioning

confidence: 99%

An NMR kinetics experiment

Kaufman¹,

Sterner²,

Masek³

et al. 1982

J. Chem. Educ.

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A kinetics experiment is found in virtually all undergraduate physical chemistry laboratory texts and indeed is even common in many organic laboratory texts. Furthermore, increasing applications of various spectrophotometric methods, particularly nuclear magnetic resonance, are being made a part of the laboratory experience in both of these courses. Thus, a kinetics experiment utilizing NMR spectroscopy to obtain rate data should be particularly attractive to instructors in these laboratories. Advantages of the ExperimentThe experiment presently discussed also offers the following advantages:1. The reactant, p-methoxyphenylacetylene, is easily synthesized from readily available starting materials.* 1 2. As little as 30 mg of compound is required per student or pair of students. 3. Other than the NMR spectrometer, the only required apparatus includes an analytical balance, syringe, NMR tube in which the entire reaction is conducted, and a temperature controlled water bath (optional). 4. The reaction involved, the hydration of an alkyne, is simple and should be known to all students who would be conducting the experiment. 5. The experiment gives reproducible data from which a rate expression is easily extracted which is consistent with the accepted mechanism of the reaction.6. The reaction is conveniently run at elevated temperatures of one's choosing and thereby permits the calculation of the energy of activation for the reaction.

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Diels-Alder Reactions of trans-4,4,4-Trifluorocrotonic Acid. II

Cited by 8 publications

References 0 publications

Stereochemistry of the Diels-Alder Reaction.

Stereochemistry of the Diels-Alder Reaction.

Stereospecific synthesis of racemic cis- and trans-6-trifluoromethylshikimic acids

An NMR kinetics experiment

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