Pericyclic chemistry of spiro[2.4]hept-2-yne

ORGN 119

Guilan Pan, pangl@mail.utexas.edu and John C. Gilbert, jgilbert@mail.utexas.edu. Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712
To address the issue of whether the [2+2] cycloaddition products from cyclopentyne are the result of [2+1] cycloaddition to a cyclopropylcarbene followed by ring expansion or by a direct process of the classical [2+2] variety, spiro[2,3]hexan-4-one is prepared and used as the penultimate precursor for a novel type of probe for defining the nature of cyclopentyne and its [2+2] cycloadducts. The results of this study will be discussed.