A Case History of Unplanned Development of New Chemistry

Abstract

A considerable part of the new chemistry of cyclohutane derivatives which has been developed over the last 30 years, including that of cyclohutenones, cyclohntadienoquinones, hydroxycyclohutadienoquinones (the strongest known neutral C,H,O acids), squaric acid, and so on, depended on the discovery that the structural unit =C-CF_2- in cyclobutene derivatives could he hydrolyzed in concentrated sulfuric acid solution to =C-C(=O)-. The development of this reaction as a synthetic procedure owes much to a fortunate accident and provides an amusing illustration of why one should not ignore what fate is determined to thrust upon you. Too often the scientific papers describing discoveries omit the story of what really happened.

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