Allene is an intrinsically chiral molecule that is one of the most underused functional groups in organic synthesis.  Addition of organocuprates to activated propargyl alcohols is the most common method employed for the synthesis of allenes.  In this poster, we will present our efforts towards development of a new radical methodology for the synthesis of allenes. Instead of using toxic organotin to initiate the radical reaction, triethylborane is used as the radical initiator.  The utilization of triethylborane or other organoboranes as radical initiators for conjugated addition to activated propargyl alcohols provides a greener alternative. Unlike the organocuprate reactions that are done under anhydrous and inert conditions, these reactions can be done in a vial open to the atmosphere.  Initial results for the addition of alkyl radicals to activated propargyl alcohols and alkynoates will be presented.

Development of a new radical methodology for the synthesis of allenes

246th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.