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Kinetics and Mechanism of 1,3-Dipolr CycloadditionsExtended version of a lecture given at the Annual Meeting of the Dechema in Frankfurt/Main on June 14th, 1962, and of the Max Tishler Lecture at Harvard University on December 10th, 1962. (1963)

Huisgen, R.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 2 (1963), S. 633-645

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ISSN: 0570-0833

Keywords: Kinetics ; Dipolar cycloaddition ; Cycloaddition ; Heterocycles ; Reaction mechanisms ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Criteria for the mechanism of 1,3-dipolar cycloadditions which lead to 5-membered rings are provided by the stereoselectivity observed with cis-trans isomeric dipolarophiles, by the effect of solvent and substituents on the rate constants, by the activation parameters, and by orientation phenomena. A concerted addition, which can also be described in terms of molecular orbitals and in which the two new σ-bonds are formed simultaneously, although not necessarily at equal rates, offers the best explanation of the experimental facts.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196306331

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1,3-Dipolar Cycloadditions. Past and FutureExtended version of lectures given at the Chemists' Meeting in Vienna (Austria) October 1961, and at the Gordon Research Conference, New Hampton (U.S.A.), 1961. (1963)

Huisgen, Rolf

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 2 (1963), S. 565-598

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ISSN: 0570-0833

Keywords: Dipolar cycloaddition ; Cycloaddition ; Heterocycles ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: In contrast to the very large number of special methods applicable to syntheses in the heterocyclic series, relatively few general methods are available. The 1,3-dipolar addition offers a remarkably wide range of utility in the synthesis of five-membered heterocycles. Here the “1,3-dipole”, which can only be represented by zwitterionic octet resonance structures, combines in a cycloaddition with a multiple bond system - the “dipolarophile” - to form an uncharged five-membered ring. Although numerous individual examples of this reaction were known, some even back in the nineteenth century, fruitful development of this synthetic principle has been achieved only in recent years.

Additional Material: 4 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196305651

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