Trimethyl Trichlorohemimellitate from an Unusual Fragmentation Reaction

Diekmann, J.

doi:10.1021/jo01045a504

Cited by 12 publications

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Carbene durch thermische Cycloeliminierung

Hoffmann

1971

Angewandte Chemie

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Das zunehmende Interesse an Carbenen verlangt Methoden, mit denen man diese Zwischenstufen in unimolekularen Zerfallsprozessengegebenenfalls in der Gasphaseohne storende Nebenprodukte erzeugen kann. Dazu haben sich neben dem Zerfatl von Diazoverbindungen thermische Cycloeliminierungen aus Carbo-und Heterocyclen ungerader Gliederzahl bewahrt. I n diesem Fortschrittsbericht werden Probleme, strukturelle Voraussetzungen und Anwendungsbreite derartiger Cycloeliminierungsreaktionen diskutiert. Am Beispiel der anderweitig nur sehr schlecht zuganglichen Dialkoxycarbene lassen sich die Vorteile der Carbenerzeugung durch thermische Cycloeliminierung aufzeigen.Angew. Chem. / 83. Jahrg. 1971 Nr. 16

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Carbene durch thermische Cycloeliminierung

Hoffmann

1971

Angewandte Chemie

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Generation of Carbenes by Thermal Cycloelimination

Hoffmann

1971

Angew. Chem. Int. Ed. Engl.

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The growth of interest in carbenes has led to a need for methods that allow their generation in unimolecular decomposition processes, possible also in the gas phase, without troublesome by-products. Besides the decomposition of diazo compounds, thermal cycloeliminations from carbocycles and heterocycles with odd numbers of ring atoms have been found to be suitable for this purpose. The problems, structural requirements, and scope of such cycloelimination reactions are discussed in the present progress report. The advantages of carbene generation by thermal cycloelimination are demonstrated with reference to dialkoxycarbenes, which are very difficult to obtain in any other way.

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Benzoannulation of Quinones by a Cycloaddition‐Fragmentation Approach. A Simple Synthesis of Methoxycarbonyl‐Substituted Polyacenoquinones

Chou¹,

Hsu²,

Chen³

2004

J Chinese Chemical Soc

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The cycloadducts 2A‐5A obtained from the Diels‐Alder cycloadditions of 1,2,3,4‐tetrachloro‐4,5‐dimethoxycyclopentadiene (1) with p‐benzoquinone (2), 1,4‐naphthoquinone (3), 1,4‐anthraquinone (4), and 2,3‐dicyano‐1,4‐benzoquinone (5) were subjected to the reaction with triethylamine in dichloromethane at room temperature. Cycloadducts 2A and 5A enolized to give the corresponding hydroquinones 2B and 5B, which were oxidized with DDQ to afford naphthoquinone ester 2D and anthraquinone ester 5D, respectively. In the cases of cycloadducts 3A and 4A, the enolization occurred concurrently with oxidation and fragmentation to produce directly the polyacenoquinone esters 3D and 4D, respectively. Under the same reaction condition, the unsymmetrical cycloadduct 6A derived from naphthoquinone ester 2D and 1 yielded isomeric polyacenoquinone esters 6Da and 6Db in a ratio of about 8:1.

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Trimethyl Trichlorohemimellitate from an Unusual Fragmentation Reaction

Cited by 12 publications

References 0 publications

Carbene durch thermische Cycloeliminierung

Carbene durch thermische Cycloeliminierung

Generation of Carbenes by Thermal Cycloelimination

Benzoannulation of Quinones by a Cycloaddition‐Fragmentation Approach. A Simple Synthesis of Methoxycarbonyl‐Substituted Polyacenoquinones

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