ORGN 311 |
| Dina C. Merrer, Ekaterina Zelenova, Marina Khrapunovich, Diana Huang, Lillian Seu, and Alexis N. Sabo. Department of Chemistry, Barnard College, 3009 Broadway, New York, NY 10027 |
| This project investigates the regioselectivities of singlet carbene additions to strained benzannelated rings. Halocarbenes :CX2 and MeCX (X=Cl, Br) have been reacted with substituted benzocyclopropenes (R1=H, Br, CHO, Me) to produce benzocyclobutene products (Eq. 1). Benzocyclobutenones (R2=H, OMe, CN) have similarly been reacted with dialkoxycarbenes MeOCOR3 (R3=Me, Ph), generating substituted indanones (Eq. 2). We will show that the regioisomeric product distributions of these two types of reactions depend upon the electron-withdrawing or electron-donating capabilities of the aryl substituents. The relationships between the substituents and the product distributions provide insight into the mechanisms of these carbene additions. |
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Physical Organic, Combinatorial, Materials, Molecular Recognition
8:00 PM-10:00 PM, Tuesday, March 30, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |
