New Synthesis Route for 1,1,2,2-Tetracyanocyclopropanes
Abstract
One,1-Dimethoxy-2-bromoethylene 1 reacts with tetracyanoethylene (TCNE,3) at -10 C to form methyl 2,2,3,3-tetracyanocyclopropanecarboxylate 6 in high yield. A similar reaction occurs with 1,1-diethoxy-2-bromoethylene 2 to yield ethyl 2,2,3,3-tetracyanocyclopropanecarboxylate 7. Further, Beta-bromoethyl 2,2,3,3-tetracyano-1-methylcyclopropanecarboxylate 10 and Beta-bromoethyl 2,2,3,3-tetracyano-1-ethylcyclopropanecarboxylate 11 were obtained by reacting TCNE with 2-bromomethylidene 8 and 2-bromoethylidene-1, 3-dioxolane 9, respectively. A reaction mechanism via a zwitterion and intra-molecular displacement of bromide is proposed.
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 01, 1990
- Accession Number
- ADA219505
Entities
People
- H. K. Hall Jr.
- Ju-yeon Lee
Organizations
- University of Arizona