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Cycloaromatization of Open and Masked 1,3‐Hexadien‐5‐ynes − Mechanistic and Synthetic Aspects
Author(s) -
Zimmermann Gerhard
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200102)2001:3<457::aid-ejoc457>3.0.co;2-b
Subject(s) - chemistry , benzene , competition (biology) , computational chemistry , organic chemistry , biology , ecology
The discovery of the net‐cyclization of 1,3‐hexadien‐5‐yne to benzene at temperatures around 250 °C was followed, particularly during the 1990s, by an increasing number of investigations of the ability of other compounds possessing a 1,3‐hexadien‐5‐yne substructure to cycloaromatize. This has led to remarkable syntheses of compounds with very interesting molecular structures and, in particular, to pronouncedly bowl‐shaped, nonalternating PAHs, the carbon skeletons of which represent fullerene subunits. Substantial insights into the three mutually exclusive cycloaromatization mechanisms, operating in distinct temperature ranges, are presented in this paper, together with the development of the method that has made it possible, when the temperature range used results in competition between the entirely different mechanisms, to analyze the complex reaction behavior.