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New Reactions of Alkylidenephosphoranes and their Preparative Uses. Part I: The Acid-Base Character of Phosphonium Salts and AlkylidenephosphoranesParts II and III will appear shortly in this journal. (1965)

Bestmann, H. J.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 4 (1965), S. 583-587

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ISSN: 0570-0833

Keywords: Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Phosphonium salts may be regarded as Bronsted acids, and alkylidenephosphoranes as the conjugate bases. Compounds of the two classes exist in equilibrium with each other. Phosphonium salts and alkylidenephosphoranes can be obtained by this “transylidation”. Other methods are also given for the preparation of members of both classes.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196505831

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New Reactions of Alkylidenephosphoranes and their Preparative Uses. Part II. Alkylidenephosphoranes and Halogen CompoundsFor Part I see Angew. Chem. 77,609 (1965), Angew. Chem. internat. Edit. 4, 583 (1965). Part III will appear shortly in this journal. (1965)

Bestmann, H. J.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 4 (1965), S. 645-660

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ISSN: 0570-0833

Keywords: Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The reaction of alkylidenephosphoranes with compounds containing halogens can be used to prepare ylides, which can be converted in to useful products, e.g. by hydrolysis, by thermal decomposition, or by other reactions. Examples of such products are ketones including cyclic, unsaturated, and branched-chain ketones (including cyclic, unsaturated, and branched-chain ketones), carboxlic esters (including those of unsaturated, branched- chain, polyenecarboxylic, acetylenecarboxylic, and allenecarboxylic acids), and aldehydes.

Additional Material: 10 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196506451

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New Reactions of Alkylidenephosphoranes and their Preparative Uses IIIFor Part I, see Angew. Chem. 77, 609 (1965) Angew. Chem. internat. Edit. 4, 583 (1965); for Part II, see Angew. Chem. 77, 651 (1965); Angew. Chem. internat. Edit. 4, 645 (1965).. Alkylidenephosphoranes and Reagents Containing Multiple Bonds (1965)

Bestmann, H. J.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 4 (1965), S. 830-838

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ISSN: 0570-0833

Keywords: Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: A few examples of preparatively useful syntheses using alkylidenephosphoranes and substances containing a C—N or C—C double bond are the preparations of olefins, allenes, pyran derivatives, and cyclopropane derivatives. Olefins, ketones, and monocyclic compounds can be obtained by autoxidation of alkylidenephosphoranes; α, β-dioxo compounds (including cyclicones) can be prepared by oxidation with peroxy-acids. Alkylidenephosphoranes can also be used for the synthesis of azines and Schiff bases. Of the many possibilities offered by the Wittig reaction, only the preparation of tritiated aldehydes and olefins will be considered.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196508301

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