Abstract
Abstract Small-ring heterocycles are an important class of penta-coordinate phosphorus compounds, whose properties—including thermolysis—have been extensively studied.1,2 It is noteworthy that these compounds display a wide range of thermal stability—certain examples decompose completely below -40°C, while others are stable indefinitely at > 300°C—yet any thermolysis reaction almost invariably takes place at the phosphorus centre. Diverse conditions have been employed: reactions have been carried out in the melt, in solution and in the gas phase, and ionic, radical and concerted mechanisms have been advanced to explain the results. In this article, we hope to rationalise this behaviour and to give a representative survey of the field. Unfortunately, a truly comprehensive review is literally not possible at this time, since in the older literature, P(v) intermediates are often written without evidence of their existence, or, betaine structures are assigned to species which are in fact phosphoranes. Two cla...
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