From fluoral to heterocycles: a survey of polyfluorinated iminiums chemistry

Billard, T.; Gille, Segolene; Ferry, Aurélien; Barthelemy, A.; Christophe, Carole; Langlois, Bernard R.

doi:10.1016/j.jfluchem.2004.08.007

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Cited by 12 publications

(2 citation statements)

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“…Recently, syntheses of a-trifluoromethylated piperidines [4,5] and lactams [4a,5] have been described starting from a-trifluoromethylated homoallylamine. Such a methodology has been also applied to the construction of bicyclic nitrogen compounds bearing a CF 3 moiety in the a position.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of β‐Trifluoromethylated Δ¹‐Pyrrolines

et al. 2010

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Section: Introductionmentioning

confidence: 99%

Synthesis of β‐Trifluoromethylated Δ¹‐Pyrrolines

et al. 2010

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“…Trifluoroacetaldehyde ethylhemiacetal (similar to our compounds, but with an OC 2 H 5 group instead of a OCH 3 one) is often used as a precursor for fluoral . Another advantage of fluoral is that it is not involved in ozone layer depletion . Chloral, and especially, chloral hydrate is a famous compound, both for its use and abuse.…”

Section: Introductionmentioning

confidence: 99%

A theoretical study of hemiacetal formation from the reaction of methanol with derivatives of CX₃CHO (X = H, F, Cl, Br and I)

Azofra

Alkorta

Elguero

2012

J of Physical Organic Chem

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A theoretical study of the hemiacetal formation reaction between methanol and CX 3 CHO (X = H, F, Cl, Br, and I) has been carried out using density functional theory and Becke, three-parameter, Lee-Yang-Parr/6-311++G(d,p) computational methods. The stationary points of the reaction between the isolated molecules and the reaction catalyzed by an additional methanol molecule have been characterized. Because the final products present a stereogenic center, the potential autocatalysis of the reaction has been examined and also the possibility of spontaneous generation of chirality when the hemiacetal molecules are involved in the transition state structure. High barriers are found in the reaction between the isolated molecules that are reduced by the assistance of an additional molecule (methanol or hemiacetal product). The reactions catalyzed by the hemiacetal products show higher barriers than the one catalyzed by methanol.

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