Histamine Antagonists. γ,γ-Disubstituted N,N-Dialkylpropylamines<sup>1</sup>

Sperber, Nathan; Papa, Domenick; Schwenk, Erwin; Sherlock, Margaret H.; Fricano, Rosemarie

doi:10.1021/ja01156a078

Cited by 38 publications

(13 citation statements)

References 3 publications

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“…3 The 13C nmr spectrum in CDC13 at -30° confirmed the presence of two distinct species in solution. Par ticularly noteworthy were two peaks at -337.72 and -335.20 ppm, relative to TMS, which established that both species contained carbene carbon atoms.…”

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confidence: 84%

“…Intensity data were collected on an automatic Picker four-circle diffractometer within the angular limits 0 < 26 < 45°, 0 < < /> < 360°, -90° < x < 90° using Mo K a radiation. The data (3) At the concentration used in the variable temperature study (52.8 mg ml-1), the dimer peak above -25° was of low and not easily mea surable intensity and decreased to zero before ambient temperature was reached. This was not a process of peak coalescence.…”

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confidence: 91%

“…The molecular structure of [Me>GeRe(C0 )4C(0 )lVIe]2.10 Selected bond lengths (A) are: Re-Ge = 2.591(3); Ge-05' = 1.96(2); C5-05 = 1.27(3); Re-C5 = 2.14(3); av Re-C(l-4) = 1.92(3); av C(l-4)-0(l-4) = 1.15 (3). Selected bond angles (deg) are: Re-C5-C8 =111 (2); Re-C5-05 = 121 (2); C8-C5-05 = 128 ( 2); Ge-05'-C5' = 139 (2), Ge-Re-C5 = 82.8 (6); Re-Ge-05' = 107.6(4).…”

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confidence: 99%

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Chirality in polyisocyanides

Nolte¹,

Beijn²,

Drenth³

1974

J. Am. Chem. Soc.

193

113

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confidence: 84%

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confidence: 91%

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confidence: 99%

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Chirality in polyisocyanides

Nolte¹,

Beijn²,

Drenth³

1974

J. Am. Chem. Soc.

193

113

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“…The solid was dissolved in benzene and stirred with charcoal overnight at rt. After evaporation of solvent, the residue was recrystallized from hexane and dried in vacuo to give 15i (23.4 g, 34 %) as a white solid; mp 62 -63 °C (ref41 65 -66 °C). 1 H NMR (300 MHz, Chloroform-d) δ 8.64 (d, J = 4.8 Hz, 2H), 7.29 (t, J = 4.8 Hz, 1H).…”

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confidence: 99%

Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations

et al. 2015

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A series of monosubstituted pyrimidinium and pyrazinium triflates and 3,5-disubstituted pyridinium triflates were prepared and tested as simple catalysts of oxidations with hydrogen peroxide, using sulfoxidation as a model reaction. Their catalytic efficiency strongly depends on the type of substituent and is remarkable for derivatives with an electron-withdrawing group, showing reactivity comparable to that of flavinium salts which are the prominent organocatalysts for oxygenations. Because of their high stability and good accessibility, 4-(trifluoromethyl)pyrimidinium and 3,5-dinitropyridinium triflates are the catalysts of choice and were shown to catalyze oxidation of aliphatic and aromatic sulfides to sulfoxides, giving quantitative conversions, high preparative yields and excellent chemoselectivity. The high efficiency of electron-poor heteroarenium salts is rationalized by their ability to readily form adducts with nucleophiles, as documented by low pKR+ values (pKR+ < 5) and less negative reduction potentials (Ered > -0.5 V). Hydrogen peroxide adducts formed in situ during catalytic oxidation act as substrate oxidizing agents. The Gibbs free energies of oxygen transfer from these heterocyclic hydroperoxides to thioanisole, obtained by calculations at the B3LYP/6-311++g(d,p) level, showed that they are much stronger oxidizing agents than alkyl hydroperoxides and in some cases are almost comparable to derivatives of flavin hydroperoxide acting as oxidizing agents in monooxygenases.

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“…Incidentally, it is of interest to note that Grignard reagents have effected the following unusual transformations: conversion of diphenyldimethylaminomethylacetonltrile into diphenylacetonitrile, 18 ethyl diphenyldimethylaminomethylacetate into l,l-diphenyl-2-butanone18 and ß,ß'-bis-(1-piperidyl)-pivalophenone into l-(l-piperidyl) -2-methyl-3-phenyl-3-pentanol (J. J. Denton, V. A. Lawson, W. B. Neier and R. J. Turner, ibid., 71, 2050 (1949).…”

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confidence: 99%