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Isonitrile Syntheses (1965)

Ugi, I. ; Fetzer, U. ; Eholzer, U. ; [et al.]

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 4 (1965), S. 472-484

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ISSN: 0570-0833

Keywords: Formamides ; Synthetic methods ; Isocyanides ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: In spite of the large number of reactions which involve the formation of isonitriles, the only preparative routes to these compounds, until recently, were the classical isonitrile syntheses discovered about one hundred years ago by Gautier and Hofmann. These methods are not generally applicable, and give satisfactory yields only in exceptional cases. Isonitriles have recently become readily available by the elimination of water from N-substituted formamides, using acyl halides of Group IV-;VI elements in the presence of bases as dehydrating agents. A dehydrating system with a particularly wide range of application consists of phosgene with tertiary amines. This system generally provides the easiest and most productive route to isonitriles, particularly where large quantities (〉 1 mole) are to be prepared.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196504721

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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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The Use of Silylation in Organic SynthesesThe articles of the previous three series have been collected and published in three volumes in German by Verlag Chemie, Weinheim, Bergstr. (Germany); and in English by Academic Press, New York-London. (1965)

Birkofer, L. ; Ritter, A.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 4 (1965), S. 417-429

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ISSN: 0570-0833

Keywords: Silylation ; Synthetic methods ; Trimethylsilyl group ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The term silylation is used to denote the introduction of a triorganosilyl moiety, especially the trimethylsilyl species, into organic compounds. - Silylated amino acids and sugars are particularly suitable for the syntheses of peptides and saccharides, respectively, since the silyl group can be cleaved off readily under mild conditions. Many diamines undergo ring closure, e.g. with phosgene, only after silylation. - O-silylated lactim ethers (i.e. cyclic imino ethers) are converted into N-alkyl derivatives by alkyl halides. Compounds with a strongly polarized Si—C bond may be used for chain extension. Silyl esters of halogeno fatty acids yield lactones with silver cyanate. - Trimethylsilyl azide is thermally very stable and behaves like organic azides. It reacts with acetylenic compounds, trialkylphosphines, and triarylphosphines to yield silylated triazole derivatives, trialkylphosphines N-silylimines, and triarylphosphines to yield silylated triazole dervatives, trialkylphosphine N-silylimines, and triarylphosphine N-silylimines, respectively, from which the silyl groups can be removed under mild conditions.

Additional Material: 5 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196504171

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