| Autor: |
Vo DV; Department of Chemistry, University of Illinois Chicago, 845 W. Taylor St., Chicago, Illinois 60607, United States., Wu T; College of Chemistry and Materials Engineering, Wenzhou University, 325035 Wenzhou, Zhejiang Province, P. R. China., Luo Y; College of Chemistry and Materials Engineering, Wenzhou University, 325035 Wenzhou, Zhejiang Province, P. R. China., Xia Y; College of Chemistry and Materials Engineering, Wenzhou University, 325035 Wenzhou, Zhejiang Province, P. R. China., Lee D; Department of Chemistry, University of Illinois Chicago, 845 W. Taylor St., Chicago, Illinois 60607, United States. |
| Abstrakt: |
1,3-Diynyl propiolates undergo the Alder-ene reaction to generate enyne-allenes, which participate in the Diels-Alder reaction to provide products of a formal [2 + 2 + 2] cycloaromatization of three alkynes. Without an external alkyne, enyne-allene reacts with one of the alkyne moieties of 1,3-diynyl propiolate, whereas external alkynes can be used to trap enyne-allene to provide various arene products. The substituents on the dienophilic alkynes have a profound impact on their reactivity. In this Diels-Alder reaction, 1,3-diynes display higher reactivity than monoynes; thus, an excess amount (4-5 equiv) of external monoynes needs to be employed to get good product selectivity. |
