Synthesis of <i>N</i>-unsubstituted cycloalkylimines containing a 4 to 8-membered ring

Guillemin, Jean‐Claude; Nasraoui, Wafa; Gazzeh, Houda

doi:10.1039/c9cc01755k

Cited by 9 publications

(4 citation statements)

References 20 publications

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“…Guillemin et al reported carrying out the dehydrocyanation of aminonitriles to give imines by utilizing KOH in vacuo . 13 After the investigation, we found K 2 CO 3 to be an appropriate solid base for the present transformation of N -benzhydryl substrates. Thus, enantioenriched 2 was ground into a fine powder with K 2 CO 3 and the mixture was heated at 50 °C in vacuo .…”

Section: Resultsmentioning

confidence: 79%

“…1 ). In the reverse reaction, dehydrocyanation 13 proceeded stereoselectively with the loss of a stereocenter to give the corresponding enantiomorphic crystals of achiral imines. Furthermore, the inversion of the enantiomorphic crystals of an achiral compound was observed for the first time; therefore, the (+)-crystal of the imine was transformed to its enantiomorphic (−)-crystal by carrying out HCN addition and then elimination and vice versa .…”

Section: Introductionmentioning

confidence: 99%

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Chirally and chemically reversible Strecker reaction

et al. 2023

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Section: Resultsmentioning

confidence: 79%

Section: Introductionmentioning

confidence: 99%

Chirally and chemically reversible Strecker reaction

et al. 2023

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“…Oxirane-1-d. 2-Chloroethanol-1-d (1.63 g, 20 mmol) was then vaporised in a vacuum line (0.1 mbar) onto t-BuOK in powder heated to 90 o C (for similar experiments see Guillemin et al 2019). A trap cooled to −100 o C removed selectively the impurities (mainly t-butanol) and oxirane-1d was selectively condensed in a trap cooled at 77 K at a yield of 0.60 g or 67%.…”

Section: Synthesis Of Mono-deuterated Oxiranementioning

confidence: 99%

Rotational spectroscopy of mono-deuterated oxirane ($c$-C$_2$H$_3$DO) and its detection towards IRAS 16293$-$2422 B

Müller,

Jørgensen,

Guillemin

et al. 2022

Preprint

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We prepared a sample of mono-deuterated oxirane and studied its rotational spectrum in the laboratory between 490 GHz and 1060 GHz in order to improve its spectroscopic parameters and consequently the calculated rest frequencies of its rotational transitions. The updated rest frequencies were employed to detect c-C 2 H 3 DO for the first time in the interstellar medium in the Atacama Large Millimetre/submillimetre Array (ALMA) Protostellar Interferometric Line Survey (PILS) of the Class 0 protostellar system IRAS 16293−242. Fits of the detected lines using the rotation diagrams yield a temperature of T rot = 103 ± 19 K, which in turn agrees well with 125 K derived for the c-C 2 H 4 O main isotopologue previously. The c-C 2 H 3 DO to c-C 2 H 4 O ratio is found to be ∼0.15 corresponding to a D-to-H ratio of ∼0.036 per H atom which is slightly higher than the D-to-H ratio of species such as methanol, formaldehyde, ketene and but lower than those of the larger complex organic species such as ethanol, methylformate and glycolaldehyde. This may reflect that oxirane is formed fairly early in the evolution of the prestellar cores. The identification of doubly deuterated oxirane isotopomers in the PILS data may be possible judged by the amount of mono-deuterated oxirane and the observed trend that multiply deuterated isotopologues have higher deuteration rates than their mono-deuterated variants.

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“…α-Aminonitriles have been synthesized in the mid-19th century by Adolph Strecker using a multicomponent reaction . Primary α-aminonitriles are well-known and well-studied compounds involved in numerous reactions, and precursors of various species such as amino acids by acid hydrolysis, amines via a Bruylants reaction or imines by basic dehydrocyanation. − They probably played a key role on the Primitive Earth − and the simplest derivative, aminoacetonitrile, has been detected in the interstellar medium . To our knowledge, the corresponding phosphorus and arsenic derivatives have not yet been synthesized, whereas numerous functionalized phosphines and arsines were synthesized shortly after the nitrogen derivatives, such as vinylamine, , vinylphosphine and vinylarsine .…”

Section: Introductionmentioning

confidence: 99%

Primary α-Phosphino- and α-Arseno-Nitriles, Analogues of α-Aminonitriles

Ghabi,

Slama,

Hedhli

et al. 2024

Inorg. Chem.

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More than 170 years after the synthesis of α-aminonitriles by the reaction of Strecker, α-phosphinonitriles, and α-arsenonitriles have been prepared and characterized by NMR and IR spectroscopy. For the simplest derivatives, the reaction was carried out by reaction of cyanomethyltributylstannane with phosphorus or arsenic trichloride, followed by a chemoselective reduction of the dichlorophosphine and dichloroarsine formed to the corresponding primary phosphine and arsine. The phosphinoacetonitrile can be stored at −80 °C for months in its pure state, but arsenoacetonitrile decomposes at this temperature. Chiral compounds can be synthesized from C-substituted cyano-1-alkyltributylstannanes. In 1H NMR spectroscopy, these chiral phosphines and arsines display diastereotopic protons for the PH2 and AsH2 groups, a property never observed for the NH2 group of α-aminonitriles. This work paves the way for further studies on the chemistry of these compounds, including a comparative chemistry of these phosphorus and arsenic derivatives with the well-known α-aminonitriles.

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Synthesis of N-unsubstituted cycloalkylimines containing a 4 to 8-membered ring

Abstract: Primary cycloalkylimines with a 4 to 8-membered ring have been synthesized by dehydrocyanation of the corresponding α-aminonitriles.

Cited by 9 publications

References 20 publications

Chirally and chemically reversible Strecker reaction

Chirally and chemically reversible Strecker reaction

Rotational spectroscopy of mono-deuterated oxirane ($c$-C$_2$H$_3$DO) and its detection towards IRAS 16293$-$2422 B

Primary α-Phosphino- and α-Arseno-Nitriles, Analogues of α-Aminonitriles

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