The Synthesis of Unusual Organic Molecules from Azoalkanes. New analytical methods (33)
- 1 October 1980
- journal article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 19 (10) , 762-779
- https://doi.org/10.1002/anie.198007621
Abstract
The thermal or photochemical denitrogenation of azoalkanes constitutes an effective and convenient method for the preparation of unusual organic molecules, including highly ringstrained, sterically crowded, fluxional, antiaromatic and other interesting structures. The importance of this synthetic approach is that the azo linkage serves as a means of introducing the critical (usually last) bond in the complex target molecule. This article presents a cross‐section of such elegant synthetic utilization of azoalkanes for fused‐, bridged‐ and spiro‐cyclization. Our coverage of the large body of literature has been directed by the complexity and novelty of the products. Azoalkanes are usually prepared via cycloaddition of azo dienophiles to appropriate substrates.Keywords
This publication has 196 references indexed in Scilit:
- Synthesis and chemistry of cis- and trans-2,3-divinylthiiraneJournal of the American Chemical Society, 1979
- Domino Diels-Alder reactions. 6. Domino Diels-Alder cycloadditions to 9,10-dihydrofulvalene and 11,12-dihydrosesquifulvalene. A synthetic tool for the elaboration of polycondensed alicyclic systemsJournal of the American Chemical Society, 1978
- Surprises in base-catalyzed decompositions of bicyclo[4.2.1]nona-2,4,7-trien-9-one hydrazoneJournal of the American Chemical Society, 1977
- A methodology for the preparation and characterization of three-membered, potentially antiaromatic molecules. Preparation of matrix-isolated thiirene and selenireneJournal of the American Chemical Society, 1977
- Flash Thermolysis of Organic CompoundsAngewandte Chemie International Edition in English, 1977
- cis-Azoxyalkanes. 8. Concerted thermal cycloreversion of unsaturated azo N-oxidesJournal of the American Chemical Society, 1977
- Intramolecular 1,3‐Dipolar Cycloaddition ReactionsAngewandte Chemie International Edition in English, 1976
- Propellanes as stereochemical modelsAccounts of Chemical Research, 1974
- Di-.pi.-methane and oxa-di-.pi.-methane rearrangementsChemical Reviews, 1973
- Diels‐Alder‐Reaktionen I: Präparative AspekteAngewandte Chemie, 1966