Addition of dihalocarbenes to benzyl[1.1.1]propellane

ORGN 116

Dina C. Merrer, dmerrer@barnard.edu and Chantel I. Nicolas. Department of Chemistry, Barnard College, 3009 Broadway, New York, NY 10027
We will explore the mechanism of dihalocarbene addition to [1.1.1]propellanes. Specifically, our plan treats benzyl[1.1.1]propellane with :CX2 (X = Br, Cl) to determine the site of carbene attack: the strained central bond, a side bond, or both. Mechanisms proposed thus far include either a paddlane or biradical intermediate, or a path that involves simultaneous cleavage of the central and side bonds. Based on product studies, we will differentiate amongst these mechanisms.