Structure and Reactivity. I. The Oximation Rates of Some Straight-Chain and Monomethyl-Substituted Alkanones

Kletzke, Paul G.

doi:10.1021/jo01029a022

Cited by 12 publications

(4 citation statements)

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“…In light of these results, we were interested in whether our method is applicable to other natural products where the site of derivatization is far removed from the chiral center(s). For this purpose, we prepared the (+)- and (−)-isomers of chloromenthoxydiphenylsilane derivatives of N -acetyl- l -tyrosine ethyl ester ( 6 ), ( S )-citronellol ( 7 ), (5 S )-5,9-dimethyl-8-decen-1-ol ( 8 ), which we prepared from ( S )-citronellyl bromide, and 11-methyltridecanol ( 9 ).…”

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Chiral Silylation Reagents: Determining Configuration via NMR-Spectroscopic Coanalysis

2004

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[structure: see text]Derivatization with (+)- and (-)-chloromenthoxydiphenylsilane was used to determine the absolute configuration of the insect defensive agent pinoresinol (1). Although the (1)H NMR chemical shift differences of the resulting two diastereomers are small, (1)H NMR spectroscopy provided for the unambiguous assignment of the natural product's configuration. For this purpose, a new approach involving NMR spectra of mixtures of diastereomers was used. Our method resembles coinjecting mixtures of samples of known and unknown configuration in GC and HPLC.

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Chiral Silylation Reagents: Determining Configuration via NMR-Spectroscopic Coanalysis

2004

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“…A. is0% Rprim, sec, tertCOCz/fso% Rprim, sec, tertCOC2 "Preparative details are not given for ketones previously described (5). "Subscripts p, s, and t denote primary, secondary, and tertiary, respectively.…”

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“…The oximation studies previously reported (5) have been extended to alkanones of other structural types. For the purpose of this investigation the alkanones were divided into 25 classes (At-A^, Br-Bs, Cr-Cs, D, E, and F) as shown in Table I.…”

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“…Ten 2-aminothiazoles were prepared by the method of Dodson et al (2)(3)(4)(5), by the interaction of 2 moles of thiourea and 1 mole of a ketone having a methyl or a methylene group adjacent to the carbonyl group in the presence of oxidizing agents (l2, Br2, Cl2) (Method A), a-Haloketones (Table I) were also allowed to react with thiourea (1, 6, 7) (Method B); the products were identical with those prepared by the direct method. The structure and physical properties of the synthesized 2-aminothiazoles are given in Table II.…”

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Survey of alkanone reactivity based on time required for 50% oximation

Kletzke¹

1973

J. Chem. Eng. Data

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rect, but heat capacities are not available in the literature. However, we think that such a correction would not substantially modify our values of excess entropy. This view is supported by comparison with the Ga-Bi system (9) which is analogous to the Ga-Pb system in many aspects. In fact, excess entropies are positive in bismuthrich alloys (-0.07 e.u. at 90 at. % Bi) and negative at intermediate compositions (-0.2 e.u. at 30 at. % Bi). This is not surprising, because lead and bismuth are neighbors in the sixth period of the Periodic Table and have similar properties as shown in Table III. As one can see, the difference in electronegativity for Ga-Bi alloys is greater than or at least equal to that for Ga-Pb alloys. Taking into account the errors which affect the electronegativity values, one could attribute the differences of excess entropies between Ga-Bi and Ga-Pb alloys to electronic peculiarities. This seems supported by the maximum mixing enthalpy of Ga-Pb alloys which is larger than that of Ga-Bi alloys (920 and 504 cal/g-atom, respectively)• At present, we cannot regard the excess entropies of Ga-Pb alloys as more reliable than those of Predel and Stein for our assumption on Newman-Kopp law validity.Further calorimetric measurements of mixing enthalpies at 1143K should be carried out to get entropy values from direct experimental data. Literature Cited(1) Elliott, R. P., "Constitution of Binary Alloys," 1st suppl., McGraw-Hill, New York, N.Y., 1965. (2) Freeman, R. D., "Momentum Sensors," In "The Characterization of High Temperature Vapors," J.

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Carbon—nitrogen and nitrogen—nitrogen double bond condensation reactions

Sollenberger

Martin

1968

PATAI'S Chemistry of Functional Groups

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Structure and Reactivity. I. The Oximation Rates of Some Straight-Chain and Monomethyl-Substituted Alkanones

Cited by 12 publications

References 3 publications

Chiral Silylation Reagents: Determining Configuration via NMR-Spectroscopic Coanalysis

Chiral Silylation Reagents: Determining Configuration via NMR-Spectroscopic Coanalysis

Survey of alkanone reactivity based on time required for 50% oximation

Carbon—nitrogen and nitrogen—nitrogen double bond condensation reactions

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