The effect of pressure on sterically hindered Menshutkin reactions

Noble, W. J. Le; Ogo, Yoshiaki

doi:10.1016/s0040-4020(01)93053-4

Cited by 35 publications

(10 citation statements)

References 20 publications

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“…This spectrum and those of the (dialkylamine) silver complexes, which are analogous, therefore indicates a loosely bound dimer of the general structure (RH2N-Ag-NH2R)+. Minor fragmentations are observed for the amine complexes, and they may indicate contributions from covalently bonded structures which involve metal cation insertion.8 (5) Laser pulsed at 10 ns, power density ca. 5 X 107 W cm'2, repetition rate 10 Hz, combined amine pressure ca.…”

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confidence: 99%

Silver ion affinities of alcohols as ordered by mass spectrometry/mass spectrometry

McLuckey¹,

Schoen²,

Cooks³

1982

J. Am. Chem. Soc.

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confidence: 99%

Silver ion affinities of alcohols as ordered by mass spectrometry/mass spectrometry

McLuckey¹,

Schoen²,

Cooks³

1982

J. Am. Chem. Soc.

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“…Table I reports le Noble's results for the Menshutkin reaction of 2,5-disubstituted pyridines with methyl iodide (Sch. 1) [13].…”

Section: Position Of the Problem And Resultsmentioning

confidence: 99%

High pressure relief of steric inhibition in ionogenic organic reactions

Jenner¹

2004

High Pressure Research

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The pressure effect is examined in an ionogenic reaction, the phosphine-catalyzed cyanoalkylation of acrylic nitriles by primary alcohols. The increase of rate constants with pressure is enhanced with increasing chain length of the alcohol and depends on steric constraints imposed by the substituting methyl group in the acrylic compound. The pressure effect is in line with a considerable electrostriction depending on steric hindrance to ionization. Pressure is confirmed as a favorable determining factor in sterically hindered reactions.

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“…1 One of the authors (Hara) has been trying to generalize and to systematize the separation procedures in organic synthesis in order to do away with tedious traditional experimental techniques.2'3 To achieve this, a direct fractionation technique using high-performance liquid chromatography has been developed. 3 The procedure was designed to simplify and speed up isolation procedures, while providing for quantitative isolation of a highly purified product. We wish to report here an improved technique for the isolation of chromate oxidation products as an example of this scheme.…”

Section: Methodsmentioning

confidence: 99%

“…The solvolysis of a sulfonate of 6-octyn-2-ol (1, X = (CHg) with triple bond participation to give 4 and 5 (Scheme I) was reported in our laboratories in 1966,1 following our preliminary report of triple bond participation in the solvolysis of 6-heptyn-2-yl tosylate.2 Other types of triple bond participation were reported at approximately the same time. 3 The reaction of 1 to give the five-membered ring ketone 5 may be considered to be the model reaction for the formation of ring D in Johnsons' spectacular steroid syntheses involving olefinic and acetylenic cyclization. 4 The triple bond "terminator" has, in fact, been a key element in several studies from the Johnson group, since other likely terminators gave complex rearrangements, presumably involving 1,2 shifts.…”

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confidence: 99%