LXXXVIII.—Optically active derivatives of phenylaminoacetic acid

McKenzie, Alex.; Walker, Nellie

doi:10.1039/jr9280000646

Cited by 5 publications

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“…1-Imidoalkylphosphonium salts 5 were synthesized in a three-step procedure starting from α-amino acids and cyclic dicarboxylic acid anhydrides. 2-( N -Imido)alkanecarboxylic acids 6 were obtained in good to very good yields by melting phthalic or succinic acid anhydride with the corresponding amino acid at 140–170 °C, according to the McKenzie and Walker’s procedure ( Table 1 ) [ 32 ]. To the best of our knowledge, attempts at an electrochemical decarboxylative α-methoxylation of 2-imidoalkanecarboxylic acids have been reported only twice in the literature [ 33 – 34 ].…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of 2-imidoalkanecarboxylic acids 6 from α-amino acids: The synthesis of 2-imidoalkanecarboxylic acids 6 was carried out based on the modified procedure described by McKenzie and Walker [ 32 ]. The corresponding α-amino acid (10 mmol) was heated with phthalic or succinic anhydride (11 mmol) at 170 °C or 140 °C under reduced pressure for the time given in Table 1 .…”

Section: Methodsmentioning

confidence: 99%

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1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents

Adámek¹,

Mazurkiewicz²,

Węgrzyk³

et al. 2017

Beilstein J. Org. Chem.

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An effective synthesis of the hitherto unknown 1-imidoalkylphosphonium salts has been developed in the reported study. The crucial step in the method included the decarboxylative α-methoxylation of N-phthaloyl- or N-succinylamino acids to the corresponding N-(1-methoxyalkyl)imides, followed by the displacement of the methoxy group by the triarylphosphonium group through melting of the imide derivative with triarylphosphonium tetrafluoroborate. The imidoalkylating properties of the obtained 1-imidoalkylphosphonium salts were tested using the Tscherniac–Einhorn-type reaction with aromatic hydrocarbons as a model reaction. It was found that the Cα–P+ bond strength can be considerably reduced and the imidoalkylation of arenes can be markedly facilitated using 1-imidoalkylphosphonium salts derived from triarylphosphines with electron-withdrawing substituents such as tris(m-chorophenyl)phosphine, tris(p-chlorophenyl)phosphine and tris[p-(trifluoromethyl)phenyl]phosphine. Microwave irradiation also considerably facilitates the cleavage of the highly polar Cα–P+ bond.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents

Adámek¹,

Mazurkiewicz²,

Węgrzyk³

et al. 2017

Beilstein J. Org. Chem.

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Über das optisch aktive Mandelsäurenitril

Smith

1931

Ber. dtsch. Chem. Ges. A/B

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Smith: Uber dae opthch aktive Mandelsdiurenitril. 427 den Micellarreihen liegen bzw. die Faser als Lamelle umgeben, und die sich gegen Permanganat anders verhalten als die aus der schonenden Reinigung hervorgehenden Fasern. Bei dieser Ektrachtungsweise sind die Viscositats-Erscheinungen und die Faser-Festigkeit d g e r von der GroI3e der im Rontgen-Bild in Erscheinung tretenden Faser-Krystallite abhztngig als vielmehr von den Substanzen der Fasern, die sicb im Rontgen-Bild kaum merklich oder nur indirekt adern, und die bei der Reinigung entfernt werden. Diese Deutung der Faser-Eigenschaften schlieflt sicb zwanglos der Vorstellung an, die in den letzten Jahren auf Grund morphologischer Untersucbungen und auf Grund einer Untersuchung des Quellungs-Mechanismus gegeben worden ist, nach der die Cellulose-Krystallite, bzw. eine mebr oder weniger grol3e Anzahl von ihnen, durch die bei der Reinigung entfernbaren Faser-Substanzen, z. B. in Form von diinnen Hauten, umgeben sind, die einerseits die Festigkeit der Fasern und andererseits die in theoretischer Beziehung noch vollig unklaren anomalen Vimsitats-Erscheinungen der 68) K. Htss, Chemie d. Cellulose, S. 3. 323 [1928]. l) Biochem. Ztschr. 14, 238 [1908]. 8 ) Journ. chem. Soc. London 96, 1369 [Igog]. 8 ) Arch. Pharmaz. 246, 206 [1908]. 6, ibid. 247, 542 [Igog]. 7) Journ. Amer. chem. Soc. 48. 164 [ I~z I ] . 9) Biochem. Ztschr. 169, I [I925]. ' ) ibid. 247, 226 [1909]. O) Journ. h e r . chem. Soc. 34. 728 [rgIz]. lo) loc. cit. Biochem. Ztschr. 46, 7 [IgIz].

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Asymmetric carbonyl addition with the homochiral ketimine derived from (+) or (−)‐pinanone and benzylamine

Chen

Wang

et al. 1990

Chin. J. Chem.

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LXXXVIII.—Optically active derivatives of phenylaminoacetic acid

Cited by 5 publications

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1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents

1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents

Über das optisch aktive Mandelsäurenitril

Asymmetric carbonyl addition with the homochiral ketimine derived from (+) or (−)‐pinanone and benzylamine

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LXXXVIII.—Optically active derivatives of phenylaminoacetic acid

Cited by 5 publications

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1-Imidoalkylphosphonium salts with modulated Cα–P+ bond strength: synthesis and application as new active α-imidoalkylating agents

1-Imidoalkylphosphonium salts with modulated Cα–P+ bond strength: synthesis and application as new active α-imidoalkylating agents

Über das optisch aktive Mandelsäurenitril

Asymmetric carbonyl addition with the homochiral ketimine derived from (+) or (−)‐pinanone and benzylamine

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Product

Resources

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1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents

1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents