Tetrahedrane and Cyclobutadiene

Abstract

Tetra‐tert‐butyltetrahedrane—a useless molecule? In the first part of this progress report an attempt is made to answer this provoking question in order that the reader can evaluate why it is worthwhile to track such an esoteric molecule. An account of the unusual properties of tetra‐tert‐butyltetrahedrane, the only tetrahedrane unequivocally identified so far, and the most highly strained saturated hydrocarbon of all, is followed by a summary of attempts to synthesize the parent compound. The emphasis in these two sections is on our own research achievements. Since any discussion of the tetrahedranes must necessarily include the corresponding cyclobutadienes, it was found appropriate to organize the article at the same time as a final account of the cyclobutadiene problem. Masamune[8c] characterized his excellent report in 1980 in the journal Tetrahedron as a comma in the history of cyclobutadiene. Meanwhile, the significant questions have been answered. The time is now ripe to replace the comma by a full stop.