175234-01-2Relevant academic research and scientific papers
Substituent effects on intramolecular epoxide cyclizations that can competitively occur at aromatic or double bond positions
Taylor, Stephen K.,May, Scott A.,Stansby, Eric S.
, p. 2075 - 2080 (2007/10/03)
The effects of substituents on epoxides that can competitively cyclize at either a double bond or aromatic position were determined. Adding a group that would stabilize the transition state of the double bond cyclization of an epoxide that underwent predominantly aromatic cyclization increased the relative amount of the former pathway, but not dramatically. Adding a strong activating substituent to the aromatic group of an epoxide that underwent predominantly double bond cyclization increased the relative amount of aromatic cyclization, but a complex product mixture was obtained. An explanation of the behavior observed is presented.
