89210-58-2Relevant academic research and scientific papers
1,3-Dipolar Cycloadditions to Difluoroallene. The regiochemistry of Diazoalkane Additions
Dolbier, William R.,Burkholder, Conrad R.,Winchester, William R.
, p. 1518 - 1522 (2007/10/02)
The regiochemistry of 1,3-dipolar diazoalkane cycloadditions to 1,1-difluoroallene (DFA) and fluoroallene was investigated.While simple frontier orbital HOMO-LUMO interactions seem to control the ?-bond specificity with which DFA cycloadds to diazoalkanes, the orientation with which these dipoles add to DFA's C2-C3 bond varies and is determined by a balance of two factors.One is a frontier orbital interaction which in the case of allene dipolarophiles is apparently dominated by a novel secondary orbital interaction.Steric effects, however, become increasingly important as the carbon terminus of the diazoalkane becomes increasingly bulky.
