γ-Keto- and γ-Hydroxy-γ-phenylbutyramides. Synthesis, Absorption Spectra and Structure Studies

Cromwell, Norman H.; Cook, Kenneth E.

doi:10.1021/ja01550a037

Cited by 44 publications

(27 citation statements)

References 1 publication

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“…Filtration, evaporation of the solvent and column chromatography purification gave 4 as a light yellow oil (2.2 g, 61%). [13] (39): β-Benzoylpropionic acid [14] (3.6 g, 20 mmol) and N-methylbenzylamine (2.2 g, 18 mmol) were coupled with the aid of dicyclohexylcarbodiimide according to the literature procedure. [15] The crude product was purified by column chromatography and recrystallisation from ethanol to give 39 (4.9 g, 85%, mixture of rotamers).…”

Section: (E)-4-dodecen-3-one (4)mentioning

confidence: 99%

A Straightforward Synthesis of Cyclopropanes from Aldehydes and Ketones

Gandon¹,

Bertus²,

Szymoniak³

2000

Eur. J. Org. Chem.

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Section: (E)-4-dodecen-3-one (4)mentioning

confidence: 99%

A Straightforward Synthesis of Cyclopropanes from Aldehydes and Ketones

Gandon¹,

Bertus²,

Szymoniak³

2000

Eur. J. Org. Chem.

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“…2 Hayashi and Ueda et al 3 • 4 reported the synthesis of polyamide containing hydroxyl groups by the ring-opening polyaddition of 4,4' -disubstituted bis ( 4-butanolide) with HMDA. It is therefore presumed that the polycondensation of this monolactone monomer with HMDA may be accompanied by a ring-opening addition.…”

Section: Hc -O CL -Imentioning

confidence: 99%

Synthesis and Characterization of Polyamide by Interfacial Polycondensation of Dichloroformyl-Containing γ-Lactone with Hexamethylenediamine

Kimura

Morimoto

Sasaki

et al. 1990

Polym J

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ABSTRACT:(2R*,4S*)-4-chloroformyl-2-chloroformylmethyl-2,4-dimethyl-4-butanolide was prepared by the chemical transformation of I-butyl methacrylate dimer telomerized using bromotrichloromethane. The interfacial polycondensation of this acid dichloride with hexamethylenediamine was accompanined by a partial hydrolytic cleavage of the lactone ring and gave an unique 6,6-type polyamide containing both lactone rings and hydrophilic groups such as carboxyl-and hydroxyl-groups. To determine the optimal conditions for interfacial polycondensation, the influence of the following factors on yield, value of intrinsic viscosity, and ring-opening ratio of polyamide was studied: volume of phase solvent, molar ratio of diamine to acid dichloride, molar ratio of sodium hydroxide as a hydrogen chloride acceptor to acid dichloride, temperature of reaction, the kinds of hydrogen chloride acceptors and organic phases, and contribution of stirring. The resulting polyamide was highly soluble in methanol, which is a poor solvent for conventional polyamides. A transparent and flexible film prepared from the methanol solution by a casting technique had a glass transition temperature of 88°C and a water absorption of ca. 30% at 95% relative humidity. Furthermore, the carboxylato-containing polyamide modified by treatment with potassium hydroxide was very soluble in water. In previous papers, 1 we reported the free radical telomerization of methacrylate monomers using bromotrichloromethane (BTCM) as a telogen. The effects of the substituent in the ester group on the telomerization and characteristics of the resulting n: 1-[methacrylate monomer]: [BTCM] adducts were studied systema ti call y. KEY WORDS

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“…This shou-s t h a t the initial attack by methylamine is a t the carbonyl group of 111 (R = CI-13), and t h a t the intermediate lceto amide VII (B = NI-lCT-TI) which is produced cyclizes spontaneously to the pyrrolidinone. Tliese results confirrn the niost 'illany dl:ficzilties hawe arisen in tlte literatz~re (2,(7)(8)(9)(10)(11) In coiltrast t o the extreinely rapid reactions of the unsaturated lactoiles \\it11 methylamine, that of 4-hydroxypentanoic acid lactone (IV, R = CH3) \\.as slow. Isolation of the hydroxyalnide VIII (B = NI-ICH3) as the major product showed that ilucleophilic attack a t the carbonyl group had occurred (p.m.r.…”

mentioning

confidence: 95%

CARCINOGENICITY OF LACTONES: I. THE REACTION OF 4-Methylbuteno- AND 4-Methylbutano-Γ-Lactones WITH PRIMARY AMINES

Jones¹,

Young²

1966

Can. J. Chem.

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.Is the first stage in the investigations of the mecha~~isms of action of carcinoger~ic lactoiles, the reactions of 4-hydroxypent-2-enoic acid lactone (11, R = CH3), which is a carcinogen, and of the non-carcinogenic 4-hydroxypent-3-enoic (111, R = CHI) and 4-hydroxypentanoic (IV, I< = CH3) acid lactones with methylamine and benzylamine have been studied. As expected, the carcinogenic lactone reacts to give the Michael addition products, whereas both inactive lactones undergo ring opening by nucleophilic attack a t the carbonyl group. From the relative rates of reaction of the amines with the lactones it is cot~cluded that the induction of tumors by 11 (R = CH3) does not involve allcylation of biological primary allcylamino groups. The proton magnetic resonance spectra of the products enable the different reaction pathways to be distinguished readily, and may proyide the basis for rapid physicoche~nical screening of a1l;ylation agents that are potential carcinogens.

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γ-Keto- and γ-Hydroxy-γ-phenylbutyramides. Synthesis, Absorption Spectra and Structure Studies

Cited by 44 publications

References 1 publication

A Straightforward Synthesis of Cyclopropanes from Aldehydes and Ketones

A Straightforward Synthesis of Cyclopropanes from Aldehydes and Ketones

Synthesis and Characterization of Polyamide by Interfacial Polycondensation of Dichloroformyl-Containing γ-Lactone with Hexamethylenediamine

CARCINOGENICITY OF LACTONES: I. THE REACTION OF 4-Methylbuteno- AND 4-Methylbutano-Γ-Lactones WITH PRIMARY AMINES

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