The historical development of the methods to generate dehydrobenzene is outlined. Dehydrobenzene readily adds nucleophilic as well as electrophilic partners. Diels‐Alder addition to dienes is moreover a valuable synthetic principle. The intermediacy of dehydrobenzene has been proved for polar additions by labeling with 14C or with a substituent. The same conclusion has been reached in Diels‐Alder additions by competition experiments. The considerable selectivity displayed by dehydrobenzene in both types of reaction is not caused by solvation, since recently the existence of dehydrobenzene in the gas phase has been established, where it reacts similarly as in solution.
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Georg Wittig (1965) studied this question.
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