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Synlett 1997; 1997(12): 1327-1334
DOI: 10.1055/s-1997-1036
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Synthetic Equivalents of Cyclohexatriene in [4+2]-Cycloaddition Reactions: Methods for Preparing Cycloadducts to Benzene

Sergio Cossu, Fabrizio Fabris, Ottorino De Lucchi*
  • *Dipartimento di Chimica, Università Ca’ Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy, Fax Int. Code 41 529 8517; E-mail delucchi@unive.it
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Publication Date:
31 December 2000 (online)

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The methods available today to obtain the cycloadducts that would form in the reactions of dienophiles with benzene are reviewed. Amongst these methods, the one which engages 1,3-cyclohexadienes substituted at the 5 and 6 positions with removable functional groups will be discussed in more detail. Substituents must be chosen carefully so that they do not interfere with the reactivity of both dienophile and diene (if possible they should activate the cycloaddition) and so that they do not fall apart to form an aromatic molecule. Such 5 and 6 protected 1,3-cyclohexadienes can be prepared using several different methods, one of which consists of a double cycloaddition of a dienophile on properly substituted dienes. Because the overall result is the preparation of a cycloadduct performed on benzene, in the very same way as it reacted as a cyclohexatriene, these molecules can be considered as equivalents of cyclohexatriene in [4+2]-cycloaddition reactions.

benzene - cyclohexatriene - [4+2]-cycloaddition - bicyclo[2.2.2]octa-2,5-diene - Diels-Alder reaction