Normal and Abnormal Alkylation of 2-Methylcyclopentyl Methyl Ketone

Wash, George; Shive, Billie; Lochte, H. L.

doi:10.1021/ja01856a032

Cited by 5 publications

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“…-Das zur Herstellung des Oxims 10a benotigte [N-Methylpiperidyl-(2)]-phenyl-keton (16) ist schon auf einem etwas umstandlichen Weg synthetisiert worden [6]. Geeigneter erwies sich die N-Methylierung des fruher von uns beschriebenen 2-Cyanopiperidins (17a) und (2-Methylcyclopenty1)-phenyl-keton (25) wurde nach bekannter Vorschrift [7] und ausgehend von trans-(2-Methylcyclopenty1)-methyl-keton (26) [8] In Vorversuchen zeigte sich, dass nicht nur die P-Toluolsulfonate der a-Aminoketoxime 1Od und 13d, sondern auch die Benzoate 1Oc und 13c schon bei der Herstellung bei -10" fragmentiert wurden. Hingegen gelang die Isolierung der kristallinen Acetate 10b und 13b.…”

Section: Fragmentierung Von A-aminoketoximen IV Teil Der Einfluss Sunclassified

“…[7] : 48%) erhalten und nach [7] [8] SUMMARY (N-Methyl-2-piperidy1)phenyl ketoxime acetate( lob) and (N-methyl-2-pyrrolidiny1)phenyl ketoxime acetate (13b) undergo quantitative fragmentation in 80% ethanol to yield benzonitrile and the cyclic imonium salts 11 and 14. Their reaction rates are approx.…”

Section: B) a U S Trans-(z-methyzcyclohexyz)-phenyz-ketoxim ( 1 2~)mentioning

confidence: 99%

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Fragmentierung von α‐Aminoketoximen. IV. Teil Der Einfluss sterischer. Faktoren Fragmentierungsreaktion, 17. Mitteilung

Grob

Sieber

1967

Helvetica Chimica Acta

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(N‐Methyl‐2‐piperidyl)phenyl ketoxime acetate(10b) and (N‐methyl‐2‐pyrrolidinyl)‐phenyl ketoxime acetate (13b) undergo quantitative fragmentation in 80% ethanol to yield benzonitrile and the cyclic imonium salts 11 and 14. Their reaction rates are approx. 107 and 108, respectively, as high as those calculated for the homomorphous compounds, viz. 2‐methylcyclohexylphenyl ketoxime acetate (12b) and 2‐methylcyclopentylphenyl ketoxime acetate (15b), which undergo quantitative Beckmann rearrangement. Synchronous fragmentation therefore provides a very large driving force for ionisation, even when the stereo‐electronically suitable conformation is not the prevalent one, as with 10b.

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Section: Fragmentierung Von A-aminoketoximen IV Teil Der Einfluss Sunclassified

Section: B) a U S Trans-(z-methyzcyclohexyz)-phenyz-ketoxim ( 1 2~)mentioning

confidence: 99%

Fragmentierung von α‐Aminoketoximen. IV. Teil Der Einfluss sterischer. Faktoren Fragmentierungsreaktion, 17. Mitteilung

Grob

Sieber

1967

Helvetica Chimica Acta

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“…page 124; 84, page449), has been extended considerably(2,4,11,12,13, 15, 18, 34,105, 158, 159, 160, 162, 163, 169,170,171,172,185,292,293,296,544,600,601,614,661,729,760,778,798,846,869).…”

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The Chemistry of the Alkali Amides.

Levine¹,

Fernelius²

1954

Chem. Rev.

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This review of the chemistry of the alkali amides is a continuation of two earlier reviews (17) which have appeared on this subject. In the present review the authors have summarized the work on the inorganic and organic chemistry of the alkali amides which has appeared in the literature from 1937 through 1952. In addition, a considerable amount of previously unpublished material is discussed. Whenever possible, the authors have tried to interpret and evaluate critically the material presented and to call attention to those areas of research which have not been investigated or which should be studied further. Although it has not been convenient to discuss all of the present material under the same headings as were used previously, the changes have not been so extensive as to make cross references difficult.

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The Cleavage of Non‐Enolizable Ketones with Sodium Amide. TheHaller‐Bauer Reaction

Hamlin

Weston

2011

Organic Reactions

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In this chapter the Haller‐Bauer is defined as the action of sodium amide on a non‐enolizable ketone causing cleavage of a carbon‐to‐carbon bond and resulting in the formation of an amide and a hydrocarbon. Textbook definitions have limited the reaction to the alkylation of ketones in which sodium amide acts a condensing agent or have considered it a combination of the alkylation and cleavage reactions. Haller and Bauer reported the isolation of benzamide after the treatment of benzophenone with sodium amide in boiling benzene or toluene and followed this observation with an extended study of the reaction. A modification of the Haller‐Bauer reaction involving the use of a fused eutectic mixture of sodium an potassium amides has been applied to certain alicyclic and bicyclic terpenoid ketones as well as to some amides.

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Normal and Abnormal Alkylation of 2-Methylcyclopentyl Methyl Ketone

Cited by 5 publications

References 0 publications

Fragmentierung von α‐Aminoketoximen. IV. Teil Der Einfluss sterischer. Faktoren Fragmentierungsreaktion, 17. Mitteilung

Fragmentierung von α‐Aminoketoximen. IV. Teil Der Einfluss sterischer. Faktoren Fragmentierungsreaktion, 17. Mitteilung

The Chemistry of the Alkali Amides.

The Cleavage of Non‐Enolizable Ketones with Sodium Amide. TheHaller‐Bauer Reaction

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