Many bicyclic cyclopropylidenes are known to rearrange to cyclic allenes. In this project we describe the synthesis of spiropentanes such as 1  which can be used as photochemical precursors to cyclopropylidenes 2    . Rearrangement of 2  then affords the cyclic allene 3  . It is anticipated that this approach would provide a route to extremely strained cyclic allenes that are otherwise inaccessible by current methods. Computational studies that model these systems will be also described. 

Spiropentanes as sources of cyclic allenes

243rd National Meeting (2012)

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