We Study Cyclooctatetraene, Why Not Benzene

When starting this chapter we promised ourselves and the reader not to consider benzene and its derivatives. Cyclooctatetraene [or more properly (Z,Z,Z,Z)-l,3,5,7-cyclooctatetra-ene, 147] is generally recognized as a polyene and so this latter compound would appear to belong here. How can we do one and not the other Therefore, in this concluding section of the chapter, we briefly discuss the enthalpies of formation of some of the 

ANNULENES AROMATICITY AND ANTIAROMATICITY A. If We Study Cyclooctatetraene, Why Not Benzene  

Regardless of how we wish to define the resonance stabilization of the n = 6 case of benzene, it is unequivocal that this substance enjoys considerable stabilization relative to classical expectations related to acyclic and/or less unsaturated precedent. Rather than discussing the plethora of models and even greater experimental evidence that documents this aromaticity , we consider benzene itself as the paradigm. We will return to olefinic paradigms later in this section. 

More precisely, let us consider the enthalpies of reaction for the formal process 47  

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