ISSN:
0570-0833
Keywords:
Cycloelimination
;
Nitrogen cycloelimination
;
Carbenes
;
Heterocycles
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Cyclic azo compounds including heteroaromatics with a N=N bond of strong double-bond character can eliminate molecular nitrogen on addition of sufficient thermal energy or on electronic excitation. Some substrates decompose spontaneously, others are moderately or even extremely resistant to N2-elimination. From a preparative point of view this type of reaction opens a variety of interesting possibilities, e.g. the synthesis of small carbocycles or heterocycles, strained bi- and polycycles, as well as cage compounds. From a theoretical mechanistic viewpoint, current importance attaches to the primary fragments such as carbenes, diradicals, trimethylene, trimethylenemethane, dipoles, ylides, antiaromatic 4π-systems, unstable cycloalkynes, and arynes.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/anie.197708351
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